Chatham Rentals
From $503 per night (USD)VRBO
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)VRBO
From $331 per night (USD)Expedia
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)Expedia
From $538 per night (USD)VRBO
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)VRBO
From $868 per night (USD)Expedia
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)Expedia
From $661 per night (USD)VRBO
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)VRBO
From $334 per night (USD)Expedia
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)Expedia
From $362 per night (USD)VRBO
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)VRBO
From $806 per night (USD)Expedia
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)Expedia
From $804 per night (USD)VRBO
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)VRBO
From $1737 per night (USD)Expedia
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)Expedia
From $986 per night (USD)VRBO
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)VRBO
From $909 per night (USD)Expedia
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)Expedia
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 $1272 per night (USD)VRBO
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)VRBO
From $479 per night (USD)Expedia
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)Expedia
From $1076 per night (USD)VRBO
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)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 $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 $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 $1952 per night (USD)VRBO
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)VRBO
From $1222 per night (USD)Expedia
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)Expedia
From $438 per night (USD)VRBO
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)VRBO
From $1401 per night (USD)Expedia
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)Expedia
From $316 per night (USD)VRBO
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)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 $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 $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 $458 per night (USD)VRBO
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)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 $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 $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 $2450 per night (USD)VRBO
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)VRBO