Chatham Rentals
From $813 per night (USD)VRBO
Private Beach, Water Views, Incredible Location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16695 - Tide's Edge: Private Beach, Water Views, Incredible Location! The Space: Welcome to Tide's Edge, a ...
From $813 per night (USD)VRBO
From $1789 per night (USD)Expedia
Experience a relaxing vacation at this beautifully maintained estate!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Experience a relaxing vacation at this beautifully maintained estate, featuring lush gardens and mature trees. This brig ...
From $1789 per night (USD)Expedia
From $1581 per night (USD)VRBO
Experience the charm of a beautiful seaside cottage just steps from Ridgevale Beach!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the charm of a beautiful seaside cottage just steps from Ridgevale Beach! Available as a new rental for 2026, ...
From $1581 per night (USD)VRBO
From $686 per night (USD)Expedia
Spacious Dog-Friendly Retreat in Chatham
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom-3 Bathroom- Sleeps 8 During peak summer weeks it is typical for our properties to require a 7-night stay, eith ...
From $686 per night (USD)Expedia
From $1506 per night (USD)VRBO
Pet friendly, water views and lush lawns!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Views, views, views! Charming 3 bedroom, 3 bath cottage right on Mill Pond. Classic Cape Cod furnishings. Window A/C un ...
From $1506 per night (USD)VRBO
From $973 per night (USD)Expedia
Luxury Chatham Escape w/ Stunning Waterfront Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wake up to stunning waterfront views at this beautifully designed Chatham retreat. The main level features an open livin ...
From $973 per night (USD)Expedia
From $1547 per night (USD)VRBO
Walk to Famous Chatham Lighthouse Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Ideally situated in one of Chatham's most sought-after areas, just steps from Lighthouse Beach, this vacation home is ri ...
From $1547 per night (USD)VRBO
From $654 per night (USD)Expedia
New construction. Short Walk to Beautiful Ridegevale Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
New construction, more photos to come. Quiet neighborhood. Short stroll to Ridgevale Beach, sleeps 6. First floor maste ...
From $654 per night (USD)Expedia
From $732 per night (USD)VRBO
Coastal Fun in Chatham – Your Cape Cod Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Stunning Chatham Home near Beach & Rail Trail Three levels of spacious, updated accommodations. Enjoy the grill, expan ...
From $732 per night (USD)VRBO
From $733 per night (USD)Expedia
Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Tucked between Forest Beach and Pleasant Street Beach, Stone’s Throw is a light-filled 4-bedroom, 3-bath South Chatham r ...
From $733 per night (USD)Expedia
From $1318 per night (USD)VRBO
North Chatham Beachwalk -Spacious 6 bedroom walk to beach sprawling private yard
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
Sprawling Family home 3-minute walk to the beautiful Chatham Beach Relax and enjoy your summer family vacation in this s ...
From $1318 per night (USD)VRBO
From $1168 per night (USD)Expedia
Chatham Family Retreat w/ Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful 5BR Chatham home with Pool Chatham Retreat with Heated Pool, Spacious Deck & Direct Rail Trail Access Welcom ...
From $1168 per night (USD)Expedia
From $783 per night (USD)VRBO
New 3 bdrm/3b near Jackknife Beach/Wequassett/Gameroom
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Caper's Mate, a charming 3 bedroom, 3 full bath house located near Jackknife Cove, Wequassett Resort, clo ...
From $783 per night (USD)VRBO
From $567 per night (USD)Expedia
Great location, Dog Friendly, Central AC!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: 16699 - Cranberry Haus: Great location, Dog Friendly, Central AC! The Space: Get ready for your next Cape ...
From $567 per night (USD)Expedia
From $351 per night (USD)VRBO
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Sea House The Space: Tucked away among the trees at the end of a quiet lane, this light-filled cottage pro ...
From $351 per night (USD)VRBO
From $894 per night (USD)Expedia
Serene home near downtown with furnished deck - walk to Ridgevale Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Cozy Cape Time The Space: Classically Cape Cod in its style and appeal, this cozy, four-bedroom retreat in ...
From $894 per night (USD)Expedia
From $397 per night (USD)VRBO
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: A Chatham Pearl on Oyster River The Space: Experience a glimpse of Cape Cod waterfront living at this thre ...
From $397 per night (USD)VRBO
From $533 per night (USD)Expedia
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Lucky Number Seven The Space: This immaculate, sun-lit home features a spacious living room with a comfort ...
From $533 per night (USD)Expedia
From $486 per night (USD)VRBO
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: South Chatham Sunshine The Space: Beach-going families will find a welcoming retreat at this three-bedroom ...
From $486 per night (USD)VRBO
From $503 per night (USD)Expedia
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Riviera Sunset The Space: Enjoy the seaside breeze at the Riviera Sunset for your next vacation! Perfect f ...
From $503 per night (USD)Expedia
From $331 per night (USD)VRBO
Dog-Friendly Home w/Yard, Deck, Free WiFi, New Gas Grill - Walk to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Seashell Wishes-Salty Kisses The Space: Classic and comfortable in its decor and design, this home in Sout ...
From $331 per night (USD)VRBO
From $538 per night (USD)Expedia
Water-view house near golf with firepit, grill, deck, central AC & washer/dryer
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Chatham Charmer The Space: Relaxation and outdoor fun await at this charming Chatham house. Located just 0 ...
From $538 per night (USD)Expedia
From $868 per night (USD)VRBO
Home near beach & tennis/basketball court with firepit, grill, & patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: The Sea Star The Space: Conveniently located on a private lane set back from the main road and only a 1/3 ...
From $868 per night (USD)VRBO
From $661 per night (USD)Expedia
A well-appointed getaway near beach, Wifi, Gas grill, Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Chatham Retreat The Space: A well-appointed and spacious coastal getaway awaits at this stylish 3BR/2BA h ...
From $661 per night (USD)Expedia
From $334 per night (USD)VRBO
Friendly retreat with a deck, AC, and board games - stellar central location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Corner Cottage The Space: Charm, wonder, and fun await in Chatham. This family-friendly home, that's been ...
From $334 per night (USD)VRBO
From $362 per night (USD)Expedia
New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Charming Downtown Chatham Condo The Space: A lavish coastal getaway awaits at this brand-new 1BR condo, bo ...
From $362 per night (USD)Expedia
From $806 per night (USD)VRBO
Waterfront house on Bucks Creek Marsh with deck, dock, & kayaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Magnificent Salt Waterfront with Sunset & Views The Space: On the saltwater inlet of Bucks Creek Marsh wit ...
From $806 per night (USD)VRBO
From $804 per night (USD)Expedia
Waterfront Home Overlooking Taylor's pond (2417)
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience a true Cape Cod getaway in this charming coastal home, perfectly set on the tranquil waters of Taylor’s Pond. ...
From $804 per night (USD)Expedia
From $1737 per night (USD)VRBO
Three Buoys: 739-C Stunning Newly Built Custom Compound in Chatham with a Resort-Style Ambiance
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 12
This property is professionally managed by Pretty Picky Properties Stunning Newly Built Custom Compound in Chatham with ...
From $1737 per night (USD)VRBO
From $986 per night (USD)Expedia
Waterfront Escape, Game Room, Dog Friendly!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: 16700 - The Wind Drifter: Waterfront Escape, Game Room, Dog Friendly! The Space: The Wind Drifter awaits y ...
From $986 per night (USD)Expedia
From $909 per night (USD)VRBO
Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
🏡 Push open the front door as sunlight fills the rooms, with beds made up of crisp white linens and lovely finishes thr ...
From $909 per night (USD)VRBO
From $1272 per night (USD)Expedia
Waterfront Chatham Escape, Pet Friendly, Pond Views & Beach Nearby
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
4 Bedroom - 4.5 Baths - Sleeps 10 During peak summer weeks, our properties typically require a 7-night stay, either Frid ...
From $1272 per night (USD)Expedia
From $479 per night (USD)VRBO
Stevie, The Cape Farmhouse
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relaxed Cape Escape near Bucks Creek & Ridgevale Beach Welcome to your Cape Cod getaway in Chatham. This two-story home ...
From $479 per night (USD)VRBO
From $1076 per night (USD)Expedia
Close to kid-friendly Ridgevale Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just up the road from kid-friendly Ridgevale Beach! Recently redecorated and renovated Cape style house located on a qui ...
From $1076 per night (USD)Expedia
From $1699 per night (USD)VRBO
Pool, Hot Tub, Water Views and more!
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 18
Summary: 16697 - Ultimate Escape: Pool, Hot Tub, Water Views and more! The Space: Welcome to the Ultimate Escape, t ...
From $1699 per night (USD)VRBO
From $1411 per night (USD)Expedia
Luxury Home with Pool, Hot Tub & Water View
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: 16696 - Kingdom on the Cove: Luxury Home with Pool, Hot Tub & Water Views The Space: Discover a serene an ...
From $1411 per night (USD)Expedia
From $1031 per night (USD)VRBO
New! Luxury Home near town, beach, and private lake access!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
New to VRBO! Welcome to your ultimate Cape Cod getaway. Nestled in a highly desirable Chatham area, this newly listed, h ...
From $1031 per night (USD)VRBO
From $1083 per night (USD)Expedia
Bring Fido! Spacious 2 family home 7-bedroom 5 bathroom in charming Chatham.
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 15
New listing Fido friendly 7-bedroom fabulous house in Chatham. 2 family home booked out as one booking. With 5 bathrooms ...
From $1083 per night (USD)Expedia
From $820 per night (USD)VRBO
New Listing! Charming 1br house downtown Chatham, walk to beach, shops, dining.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This house has been lovingly restored by my son and I. We are so happy with the way it turned out! Along with all of the ...
From $820 per night (USD)VRBO
From $1952 per night (USD)Expedia
Original School House in the Heart of Chatham
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Built in 1869 as the Old Village Elementary School, this storied property has been transformed into a distinctive Cape C ...
From $1952 per night (USD)Expedia
From $1222 per night (USD)VRBO
Spacious 4BR house in perfect Chatham with AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Enjoy the best of Chatham! Just 1.5 miles to Downtown, this Cape home offers peace and convenience. Walk down the street ...
From $1222 per night (USD)VRBO
From $438 per night (USD)Expedia
Dog Friendly, Game Room, Central AC!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16698 - Sandy Buoys: Dog Friendly, Game Room, Central AC! The Space: Your Cape Cod adventure starts at San ...
From $438 per night (USD)Expedia
From $1401 per night (USD)VRBO
Chatham Calling... Close to Town & Bocce
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Chatham Calling... Close to Town & Bocce Compliment your Chatham get-away with accommodations of the highest caliber. T ...
From $1401 per night (USD)VRBO
From $316 per night (USD)Expedia
Cape Cod Cottage near Beaches & Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 Bedroom - 1 Bath - Sleeps 4 During peak summer weeks, it is typical for our properties to require a 7-night stay, Frid ...
From $316 per night (USD)Expedia
From $1255 per night (USD)VRBO
Walk to Schoolhouse Pond!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this beautifully updated three-bedroom dog friendly home, located within walking distance of the beloved swimmi ...
From $1255 per night (USD)VRBO
From $598 per night (USD)Expedia
Charming Dog Friendly North Chatham Ranch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Space: Welcome to your perfect slice of Cape Cod in scenic North Chatham! This charming single-story ranch features ...
From $598 per night (USD)Expedia
From $344 per night (USD)VRBO
Central AC, Game Room, Dog-Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 16701 - Happy Ours: Central AC, Game Room, Dog-Friendly! The Space: Welcome to Happy Ours, where your Cape ...
From $344 per night (USD)VRBO
From $458 per night (USD)Expedia
Close to private beach with ocean views
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedrooms - 1 Bathroom - Sleeps 6 During peak summer weeks, it is typical for our properties to require a 7-night stay, ...
From $458 per night (USD)Expedia
From $701 per night (USD)VRBO
South Chatham Gem - .4 Mile to Pleasant Street Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to this charming Chatham Cape, perfectly located for exploring all that Cape Cod has to offer. This 2-bedroom, 2- ...
From $701 per night (USD)VRBO
From $2450 per night (USD)Expedia
AMAZING NEW HOME, STEPS FROM LIGHTHOUSE BEACH!
- Bedrooms:
- 11
- Bathrooms:
- 7
- Sleeps:
- 14
Click for Drone Tour RECENTLY REDUCED BY $5000 ..... NEW RATE FOR REMAINING WEEKS IN JULY AND AUGUST, $15,000 !!! ...
From $2450 per night (USD)Expedia
From $821 per night (USD)VRBO
New 2026 Private Two-Acre North Chatham Escape with Marsh Views, Decks, and a Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Breathtaking architecture, soaring windows, and serene surroundings just minutes from downtown Chatham and wor ...
From $821 per night (USD)VRBO
From $492 per night (USD)VRBO
Luxury Chatham Retreat. Walk to Main St & Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Ditch the car and dive into the quintessential Chatham lifestyle. > Perfectly situated, this impeccably designed 2-bedro ...
From $492 per night (USD)VRBO
From $1817 per night (USD)VRBO
NEW Firepit, Outdoor Dining, Large Yard, Office & More!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Mariners Horizon, a newly renovated Chatham retreat perfect for families, groups, and remote workers. Relax a ...
From $1817 per night (USD)VRBO
From $872 per night (USD)VRBO
Charming Chatham Cottage - Walk to Main St, Chatham Bars Inn & Oyster Pond Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Walk to Downtown Chatham, Beaches & Cape Cod's Best Spots Welcome to your perfect Cape Cod getaway. Nestled on a quiet ...
From $872 per night (USD)VRBO
From $618 per night (USD)VRBO
Water View Chatham Retreat by White Pond and Bike Trail
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautifully maintained home offers stunning lake views and captures the essence of Cape Cod relaxation. Located di ...
From $618 per night (USD)VRBO
From $1292 per night (USD)VRBO
NEW Close to Downtown Chatham & Oyster Pond - Game Room & Spacious Deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Oyster Pond Retreat, a spacious Chatham getaway perfect for families and groups looking to experience the bes ...
From $1292 per night (USD)VRBO
From $2085 per night (USD)VRBO
Large 5-bdrm oceanfront estate on Monomoy National Wildlife Refuge, pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Unwind in Chatham at this one of a kind estate situated on Morris Island whch is part of the Monomoy National Wildlife R ...
From $2085 per night (USD)VRBO
From $592 per night (USD)VRBO
Renovated 3-bedroom house with 2 lofts in Chatham / 4 min walk to Pleasant beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Chatham is waiting for you at this 3-bedroom house. Inside, guests find two queen beds and two twin bed, plus a loft spa ...
From $592 per night (USD)VRBO
From $1206 per night (USD)VRBO
Waterfront private beach on freshwater pond with beach in own backyard !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront . Private beach. Sleeps 8 it has 4 bedrooms featuring 2 queen beds and 4 twin beds that can be kings . there ...
From $1206 per night (USD)VRBO
From $961 per night (USD)VRBO
Gorgeous, Dog Friendly, Central AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Dog friendly, beautiful private yard, close to downtown Chatham and beaches The Space: This home is repres ...
From $961 per night (USD)VRBO
From $1321 per night (USD)VRBO
NEW! Spacious, Deck, Ping Pong, Foosball & Firepit - Luxurious Chatham Vacation!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Chatham Vacation, a newly renovated Cape Cod retreat perfect for families, two families traveling together & ...
From $1321 per night (USD)VRBO
From $596 per night (USD)VRBO
3BR Retreat Near Forest Beach & the Cape Cod Rail Trail
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Enjoy outdoor fun and easy access to Chatham`s vibrant town center. Easily explore local beaches, restaurants, ...
From $596 per night (USD)VRBO
From $1000 per night (USD)VRBO
Chatham Charm Awaits - Family-Friendly Cottage Near Beaches & Local Attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to this delightful cottage nestled in picturesque Chatham—your perfect home base for Cape adventures! With 3 comf ...
From $1000 per night (USD)VRBO
From $1595 per night (USD)VRBO
Spacious Lakefront Escape - Perfect for Families
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to our spacious lakefront home, perfect for families and large groups! With two master suites, four additional b ...
From $1595 per night (USD)VRBO
From $1211 per night (USD)VRBO
Luxury Family Fun - Heated Pool, Hot Tub, Game Room, Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home featur ...
From $1211 per night (USD)VRBO
From $1120 per night (USD)Expedia
Beautiful Chatham, Sun Sand & Surf. 8/10 mile to beaches ,pet friendly home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island view is a beautiful Chatham beach house Located in a quite cul- de- sac , think about the warm tranquil mornings ...
From $1120 per night (USD)Expedia
From $995 per night (USD)VRBO
4-bedroom house in charming Chatham steps from Main Street and the Mill Pond
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in Chatham, this charming house offers 4 bedrooms - 2 queen beds, 1 full bed, and 1 twin bed. With 2.5 bathrooms ...
From $995 per night (USD)VRBO
From $811 per night (USD)Expedia
Perfectly Content: Walk to Schoolhouse Pond
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
5 Bedroom- 3 Bathroom- Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $811 per night (USD)Expedia
From $517 per night (USD)VRBO
Charming/Great Location/Walk to town/baseball field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect location. Minute walk to town, baseball field, fish pier and beach. Bike path is right down the street. This ...
From $517 per night (USD)VRBO
From $1116 per night (USD)Expedia
Enjoy your own private pool in Chatham! (2252)
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Experience the ultimate in coastal luxury at this uniquely designed property in historic South Chatham. Perfect for larg ...
From $1116 per night (USD)Expedia
From $430 per night (USD)VRBO
Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This North Chatham 4 BR home with central AC has plenty of room for families to spread out and enjoy a relaxing Chatham ...
From $430 per night (USD)VRBO
From $705 per night (USD)Expedia
Location is Everything! Walk to 3 of North Chatham's Most Scenic Salt Water Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Location is everything! Walk to 3 of North Chatham's most scenic salt water beaches and a short trip to Chatham's covete ...
From $705 per night (USD)Expedia
From $581 per night (USD)VRBO
Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on ...
From $581 per night (USD)VRBO
From $588 per night (USD)VRBO
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy and quiet 3 bedroom, 2 bath Cape style home with an expansive, beautifully landscaped yard…the largest in the area. ...
From $588 per night (USD)VRBO
From $427 per night (USD)VRBO
Beautiful Retreat / Hot tub/ Walk to Ridgevale Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Lovely, sun-filled, completely renovated, 4 bedroom 2 full bath house located within walking distance to beautiful, kid- ...
From $427 per night (USD)VRBO
From $616 per night (USD)VRBO
PERFECT RENOVATED CHATHAM RETREAT! CENTRAL AC, COMFORTABLY SLEEPS 6!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Check in to this beautifully renovated West Chatham ranch, located south of 28 on a quiet cul-de-sac perfect for familie ...
From $616 per night (USD)VRBO
From $267 per night (USD)VRBO
Hidden Gem - Captain's Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest loc ...
From $267 per night (USD)VRBO
From $644 per night (USD)VRBO
Charming Chatham condo-Oyster Pond views, salt-water pool, tennis, water access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy the Chatham breezes off Oyster Pond and take advantage of the best the Cape has to offer whether staying on t ...
From $644 per night (USD)VRBO
From $909 per night (USD)VRBO
Home Plate Nestled in Downtown Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Description: *Four bedrooms (plus outbuilding with daybeds sleeping four and heating/cooling…great for teens!) *Beds for ...
From $909 per night (USD)VRBO
From $492 per night (USD)VRBO
Three Bedroom -- Charming, Newly Renovated Cape Cottage - Sandy, Private Ocean Beach Just 500 Ft. Away
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
harming Renovated Cape Cottage with Sandy Private Ocean Beach * * * * See end of this description for informati ...
From $492 per night (USD)VRBO
From $608 per night (USD)VRBO
Beautiful Downtown Chatham 1 Bed, Close to the Beach - Newly renovated + Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, res ...
From $608 per night (USD)VRBO
From $1185 per night (USD)VRBO
Downtown Chatham Home - Near Oyster Pond - Spacious Patio - Family Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This stunning home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, res ...
From $1185 per night (USD)VRBO
From $531 per night (USD)VRBO
Steps to Chatham Center & Lighthouse Beach - charming home with central AC
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Steps from Chatham Center and a short walk to Lighthouse Beach, our home is the perfect spot for families and couples lo ...
From $531 per night (USD)VRBO
From $921 per night (USD)Expedia
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Vivian's Hideaway! Experience all that Cape Cod has to offer in an amazing indoor and outdoor living space, n ...
From $921 per night (USD)Expedia
From $509 per night (USD)VRBO
Perfect couples escape. Close to beaches, great biking & walking & pet friendly.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This open studio apartment is the perfect stay. Privacy, beach proximity, pet friendly and CLEAN. Lots to do and see in ...
From $509 per night (USD)VRBO
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Four Bedroom home with Water Views of Saltwater Millpond & Mitchell River -- Close to Town and Oyster Pond Beach.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
3200 Square Foot Cape with Spectacular Water Views of Millpond, the Mitchell River and Stage Harbor in the Distance. * ...
Click For PricingVRBO
From $1176 per night (USD)VRBO
Spacious 4-Bedroom Home Facing Nantucket Sound
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 11
Our airy and comfortable beach house features tranquil water views, a large 22 x 11 foot elevated back deck, 4 bedrooms, ...
From $1176 per night (USD)VRBO
From $784 per night (USD)VRBO
Perfectly located, with central AC. 3BR, sleeps 6-8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our house has undergone a complete renovation with all new updates. The house has a complete master suite on the first ...
From $784 per night (USD)VRBO
From $537 per night (USD)VRBO
Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
.... PET FRIENDLY! ... Recently updated, this classic summer beach cottage is a quick walk to popular Ridgevale Beach! A ...
From $537 per night (USD)VRBO
From $1314 per night (USD)VRBO
Family Friendly Home with Private Bog View-Close to 2 beaches & town center.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Newly remodeled in 2020, this designer 4 BR, 3 full bath house sleeps 10 (8 preferred) and has everything you need to ma ...
From $1314 per night (USD)VRBO
From $931 per night (USD)VRBO
Away from it all, secluded getaway 1 mile from beach , 5 minutes to Town Center
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property offers travelers an experience like no other property in Chatham. Set back deep off of Barn Hill rd on ove ...
From $931 per night (USD)VRBO
From $619 per night (USD)Expedia
Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cape Cod style house with a large, private yard, sunny deck, outdoor shower and hammock in a quiet Chatham neighborhood. ...
From $619 per night (USD)Expedia
From $1025 per night (USD)VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachus ...
From $1025 per night (USD)VRBO
From $6623 per night (USD)VRBO
Magnificent Luxury Vacation Home in Chatham!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
This is your ultimate vacation destination! Simply stunning, Custom built home with a grand farmer's porch! Sit and sip ...
From $6623 per night (USD)VRBO
From $714 per night (USD)VRBO
CHATHAM WATER FRONT/VIEW HOUSE FIRST TIME RENTAL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect vacation spot. Enjoy your vacation on this 3 bedroom 2 bath, Central air conditioned house bordering Emery Lake ...
From $714 per night (USD)VRBO
From $641 per night (USD)Expedia
Secluded Chatham Cape Cod House Stage Harbor Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Very secluded 3br family friendly (pets considered) full Cape at the end of a cul-de-sac. Located in rural Stage Harbor ...
From $641 per night (USD)Expedia
From $1555 per night (USD)VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster. Beautifully and meticulously designed, this Town ...
From $1555 per night (USD)VRBO
From $1178 per night (USD)Expedia
Hardings Hideaway: 020-C Renovated Chatham Beach House with Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties. Renovated Chatham Beach House with Views Sl ...
From $1178 per night (USD)Expedia
From $403 per night (USD)VRBO
Lovely Stage Harbor Estate Guest House W/Private Beach to Use
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Lovely guest house on quiet and picturesque Stage Harbor! Right on town way with 30 second walk to the water and use of ...
From $403 per night (USD)VRBO
From $884 per night (USD)Expedia
Azure Cottage: Central A/C & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedrooms- 3 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $884 per night (USD)Expedia