Chatham Rentals
- From $273 per night (USD)
VRBO
Historic Cottage on White Pond, near Downtown Chatham and beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Affectionately named the "Chit-Chat", this classic 1920's 2 bedroom Cape Cod cottage is near downtown and Chatham's best ...
From $273 per night (USD)VRBO
- From $1021 per night (USD)
VRBO
A short stroll to Hardings Beach - Perfect Cape Cod Getaway Begins Here!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*Cancellation policy at end of property description.* Your search for the perfect Cape Cod getaway begins and ends ri ...
From $1021 per night (USD)VRBO
- From $530 per night (USD)
VRBO
5 Bedroom Chatham Retreat on Quiet Street
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Spacious 5 bedroom home in a great location in Chatham! This home can comfortably accommodate your entire family. Beauti ...
From $530 per night (USD)VRBO
- From $999 per night (USD)
Expedia
Relax and enjoy this stylish home in Chatham
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Picture yourself enjoying your next vacation at this newly renovated 3 bed/2.5 bath home. 4 min to beach & town. Cathedr ...
From $999 per night (USD)Expedia
- From $390 per night (USD)
VRBO
Newly Renovated and Ideally Located \/ Close to Chatham's Idyllic Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly Renovated and Ideally Located, this Two-Bedroom Home is Close to Downtown, the Chatham A's Ballpark, the Fish Pier ...
From $390 per night (USD)VRBO
- From $1286 per night (USD)
Expedia
Steps from Cockle Cove Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Steps from Cockle Cove Beach! Enjoy all the charming updates and water views in this beautifully appointed 4 bedroom (ki ...
From $1286 per night (USD)Expedia
- From $393 per night (USD)
VRBO
Coastal Condo in the Heart of Downtown Chatham!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
RECENTLY REDUCED TO $2750 PER WEEK! Coastal Condo in Heart of Downtown Chatham - Steps to Dining, Shops & Beaches A r ...
From $393 per night (USD)VRBO
- From $1870 per night (USD)
Expedia
Harbor Watch, Unique & Fabulous Home with Stunning Views on Stage Inlet!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Fabulous home on Stage Harbor Inlet. Stunning sunrise and sunset views from every room. A boaters paradise including pri ...
From $1870 per night (USD)Expedia
- From $310 per night (USD)
VRBO
Bright, sunny condo in North Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This two bedroom two bathroom sunny condo is located in the quiet neighborhood of North Chatham. A 10 minute bike ride t ...
From $310 per night (USD)VRBO
- From $620 per night (USD)
Expedia
Walk to Oyster Pond and Main Street Chatham!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16687 - Starboard Stay: Walk to Oyster Pond and Main Street Chatham! The Space: Just a steps from the tranquil ...
From $620 per night (USD)Expedia
- From $1852 per night (USD)
VRBO
Stunning Family-Friendly 7 bed - Walk to Chatham Bars Inn, Town & Beaches
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 12
This amazing seven bedroom Chatham home is located just .5 miles from Chatham’s beautiful downtown shopping area. It is ...
From $1852 per night (USD)VRBO
- From $255 per night (USD)
Expedia
Beautiful private one bedroom, just steps away from downtown Chatham!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a get-away close by Chatham's famously charming Main Street, just steps to restaurants and shops, and a short walk ...
From $255 per night (USD)Expedia
- Click For Pricing
VRBO
Renovated Chatham Compound on Bike Path, Less Than a Mile to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Recently renovated, this charming Chatham compound can sleep over 10 guests with 2 bedrooms in the main house, 2 bedroom ...
Click For PricingVRBO
- From $600 per night (USD)
Expedia
Waterfront Chatham home, walk to downtown, minutes to several beaches!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy Chatham cottage with private lake access and minutes to downtown and beaches! This house is perfect for families o ...
From $600 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Walk to Main St and Oyster Pond in Chatham!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 16685 - Chatham Breeze : Walk to Main St and Oyster Pond in Chatham! The Space: Discover the epitome of Cape C ...
From $399 per night (USD)VRBO
- From $1925 per night (USD)
Expedia
Coastal home w\/ saltwater pool, private beach access & chef's kitchen - dogs OK
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Pleasantries Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1925 per night (USD)Expedia
- Click For Pricing
Expedia
Dog-friendly home near beaches with deck, grill, firepit, streaming, W\/D, & AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bella Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired date ...
Click For PricingExpedia
- From $486 per night (USD)
Expedia
Sparkling New Build, Close to Chatham Village: 105-C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is professionally managed by Pretty Picky Properties Sparkling New Build, Close to Chatham Village Sleep ...
From $486 per night (USD)Expedia
- From $426 per night (USD)
VRBO
Updated home on large lot near Hardings Beach in S. Chatham: 040-C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is professionally managed by Pretty Picky Properties. Updated home on large lot near Hardings Beach in S. ...
From $426 per night (USD)VRBO
- From $428 per night (USD)
Expedia
Modern and Chic 3BR Home in Chatham, Close to Town: 041-CE
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is professionally managed by Pretty Picky Properties Modern and Chic 3BR Home in Chatham, Close to Town ...
From $428 per night (USD)Expedia
- From $2336 per night (USD)
VRBO
Superb Luxury Home in Chatham with New Heated Salt Water Pool: 023-CJ
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This property is professionally managed by Pretty Picky Properties Superb Luxury Home in Chatham with New Heated Salt W ...
From $2336 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Pleasant Getaway halfway between beautiful Harwichport and Downtown Chatham
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
The perfect spot for a relaxing vacation! This lovely 3+ bedroom (1 King, 3 twins, and a twin/trundle) cottage in South ...
From $450 per night (USD)VRBO
- From $1476 per night (USD)
VRBO
Panoramic Water Views w\/ Private Beach!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: 16684 - Deja View: Panoramic Water Views w/ Private Beach! The Space: Find yourself on island time at this exc ...
From $1476 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Newly renovated house 3 minutes to Wequassett Resort and 7 minutes to CBI.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upo ...
From $850 per night (USD)VRBO
- From $304 per night (USD)
VRBO
Chatham Home w\/ Spacious Deck: 2 Mi to Beaches!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience beachside bliss in Cape Cod when you stay at this 4-bedroom, 3-bath South Chatham vacation rental! This home ...
From $304 per night (USD)VRBO
- From $240 per night (USD)
Expedia
Walk to Pleasant St Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Comfortable and Charming Cottage, on a beautifully landscaped, private lot and walkable to one of Chatham's beautiful be ...
From $240 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Charming three-bedroom home in quiet neighborhood!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming three-bedroom home in quiet neighborhood! One floor living, this home offers a queen bed in each of the three ...
From $325 per night (USD)VRBO
- Click For Pricing
Expedia
The Rose Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the enchanting Rose Cottage, a hidden gem nestled in the heart of Chatham, Massachusetts. This picturesque re ...
Click For PricingExpedia
- From $675 per night (USD)
VRBO
Family & Dog friendly Chatham house with tennis &water access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Camp Moonpenny- a 3 house, 6 acre property in the Sears Point area of Chatham. While only 2 miles from Main S ...
From $675 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Chatham dog-friendly family retreat with tennis, water views & access!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Linens/towels provided. Option to book 2 adjacent houses for parties of up to 18. Available Dates 2024: May 28-Jun 15 A ...
From $625 per night (USD)VRBO
- From $642 per night (USD)
VRBO
Wonderful dog-friendly rental close to downtown Chatham and Oyster Pond Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
New for 2024!! Wonderful dog friendly rental for the whole family, with access path to a private beach deeded at White's ...
From $642 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Water Views Over Bucks Creek & Nantucket Sound
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
NEW TO THE CHATHAM RENTAL MARKET FOR 2024 Stay at this idyllic 3 bedroom 3 bath Hardings Beach Hills home with water vie ...
From $500 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Secluded North Chatham Cottage for Entire Summer [July\/August]!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Rare opportunity to spend the entire summer in North Chatham! This approximately 2,400 SF private residence is not typ ...
From $500 per night (USD)VRBO
- From $916 per night (USD)
Expedia
Heart of Chatham Village! 024-C
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties Heart of Chatham Village! New Listing for 2024! Sl ...
From $916 per night (USD)Expedia
- From $363 per night (USD)
VRBO
Cape Escape - Two Bedroom, Two Bathroom Near Beaches and Cycling
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom- 2 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $363 per night (USD)VRBO
- From $571 per night (USD)
Expedia
Chatham Cape Cod Near Bike Trail, 1 Mile to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Treat your family to a classic Cape Cod getaway at this charming Chatham vacation rental. Located 1 mile from the shore, ...
From $571 per night (USD)Expedia
- From $731 per night (USD)
VRBO
Waterfront home with lovely lake views, great deck, sun porch & fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Mill Pond Vista Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $731 per night (USD)VRBO
- From $703 per night (USD)
Expedia
On Top of Chatham, Updated, Three Level Living: 048-CH
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties On Top of Chatham, Updated, Three Level Living New ...
From $703 per night (USD)Expedia
- From $567 per night (USD)
VRBO
Sparkling Renovated Cape on Outermost Harbor, Chatham: 115-C
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This property is professionally managed by Pretty Picky Properties. Sparkling Renovated Cape on Outermost Harbor, Chath ...
From $567 per night (USD)VRBO
- From $416 per night (USD)
Expedia
Exclusive Neighborhood 1\/2 mi from Jackknife Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16671 - Whitecap: Exclusive Neighborhood 1/2 mi from Jackknife Beach The Space: Experience the quintessential ...
From $416 per night (USD)Expedia
- From $416 per night (USD)
VRBO
Amazing Family Home w\/a separate extra Cottage and Game Barn!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: 16683 - Cherry Blossom: Amazing Family Home w/a separate extra Cottage and Game Barn! The Space: Experience th ...
From $416 per night (USD)VRBO
- Click For Pricing
Expedia
Renovated 4BR Cape 10 min walk to the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Ryder's Cove Landing. Renovated 4 bedroom Cape style home . First floor features a large kitchen and dini ...
Click For PricingExpedia
- From $480 per night (USD)
VRBO
Hot Tub! Steps to Oyster Pond Beach and Downtown Chatham.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Steps to Oyster Pond Beach and Downtown Chatham from this beautifully landscaped, contemporary 3 bedroom home, located o ...
From $480 per night (USD)VRBO
- From $883 per night (USD)
Expedia
Steps from Ridgevale Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Steps from Ridgevale Beach! Enjoy spectacular and expansive water views in this beautifully appointed 3 bedroom (king, 2 ...
From $883 per night (USD)Expedia
- From $401 per night (USD)
VRBO
Short walk to beach, A\/C, pets okay, large yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedrooms - 1 Bathroom - Sleeps 4 A 3-night midweek stay - Monday to Wednesday - is offered at this home during the pea ...
From $401 per night (USD)VRBO
- From $214 per night (USD)
Expedia
Cute ranch style house on quiet road.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This sunny, cozy Cape-style ranch is a short driving distance to both Harding's and Oyster Pond beaches and the quaint v ...
From $214 per night (USD)Expedia
- From $1571 per night (USD)
VRBO
PRIVATE HEATED POOL!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private pool! Vacation near the beach in this charming 4 bedroom (King/king/queen/queen) and 2.5 bath home with private ...
From $1571 per night (USD)VRBO
- Click For Pricing
Expedia
Home near beach & tennis\/basketball court with firepit, grill, & patio
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Greenwood Lane Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For PricingExpedia
- From $811 per night (USD)
VRBO
Chatham Compound + Carriage House - Huge yard, Game Room, Kayaks, Sleeps 10
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Newly Listed to VRBO. Also listed on Airbnb, with 37 reviews and a 4.97 star rating! This beautiful family home is ever ...
From $811 per night (USD)VRBO
- From $749 per night (USD)
Expedia
NEW! Water View!! Great Location - Walk to Town, Oyster Pond Beach, Bike Path..
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Spectacular Coastal Property! Completely Reconstructed & Remodeled in 2023! Views of Oyster Pond & Short Walk to Oyster ...
From $749 per night (USD)Expedia
- From $338 per night (USD)
VRBO
Roof Deck, Walk to Forest Beach, Fire Pit!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16679 - Inn Bloom: Roof Deck, Walk to Forest Beach, Fire Pit! The Space: Inn Bloom is perched on a small hills ...
From $338 per night (USD)VRBO
- From $1118 per night (USD)
Expedia
Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friend
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16680 - Seaside Sapphire: Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friendly! ...
From $1118 per night (USD)Expedia
- From $395 per night (USD)
VRBO
Quintessential Cape directly on the Cape Cod Rail, Dog Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16682 - Nob Hill: Quintessential Cape directly on the Cape Cod Rail, Dog Friendly! The Space: In this Quintess ...
From $395 per night (USD)VRBO
- From $327 per night (USD)
Expedia
Bring your pups to Chatham! Direct access to the Cape Cod Rail Trail
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: 16681 - Summer On: Bring your pups to Chatham! Direct access to the Cape Cod Rail Trail The Space: Escape to t ...
From $327 per night (USD)Expedia
- From $1429 per night (USD)
VRBO
Enjoy a Cape Cod beach vacation on the beach in picturesque Chatham.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Have the vacation of your dreams in this oceanfront beach cottage with beautiful water views, located on Morris Island i ...
From $1429 per night (USD)VRBO
- From $751 per night (USD)
Expedia
Chatham Vacation Rental With Pool and Charm to Spare!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in one of Cape Cod’s premier resort towns, 764 Riverview Drive offers everything a discerning vacationer is look ...
From $751 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Let your Chatham traditions begin here!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
From the moment you walk into our charming single floor cottage you are invited to relax and unwind. Whether it is coffe ...
From $250 per night (USD)VRBO
- From $1386 per night (USD)
VRBO
Water views, private beach and spectacular sunsets from highest point in town.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
This large, beautiful home is the perfect place to stay for your next beach vacation: whether you’re hosting a big group ...
From $1386 per night (USD)VRBO
- From $1400 per night (USD)
VRBO
Walk to beach, ball fields, Chatham Bars Inn and town from this central location
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 12
This large, newly renovated home is the perfect spot for your Chatham getaway. It sits on a beautifully landscaped lot w ...
From $1400 per night (USD)VRBO
- From $1657 per night (USD)
VRBO
Large, beautiful home with extraordinary design features and bonus rooms galore
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 12
This large, gorgeous home is perfect for entertaining, set on an acre of land with a private yard and large patio. The h ...
From $1657 per night (USD)VRBO
- From $1575 per night (USD)
VRBO
Renovated Chatham Cape House on Cranberry Bog walking distance to Beach
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Beautifully renovated classic cape house with back deck overlooking a quintessential cranberry farm. House includes 5 be ...
From $1575 per night (USD)VRBO
- From $630 per night (USD)
VRBO
5 Bedroom Home Close to Town, Chatham Anglers, Oyster Pond, CBI with Peloton
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful and immaculate air-conditioned 5 bedroom, 2 bath home in great downtown location. Home is recently available ...
From $630 per night (USD)VRBO
- From $535 per night (USD)
VRBO
New 2024 - South Chatham Summerhouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This home is represented by Nauset Rental, a local vacation rental management company. Welcome to South Chatham Summer ...
From $535 per night (USD)VRBO
- From $559 per night (USD)
Expedia
A short drive brings you to Jackknife Cove!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy your vacation at this charming and cozy, 3 bedroom, 2 bath home. Offering 2 queens, 2 twins, and a king. Enjoy you ...
From $559 per night (USD)Expedia
- From $253 per night (USD)
VRBO
Charming 2-bedroom condo Less than 1 mile from Ridgevale Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy and relax on Cape Cod with our newly renovated condo in Chatham. Less than a mile from Ridgevale Beach. One of the ...
From $253 per night (USD)VRBO
- From $493 per night (USD)
VRBO
Waterviews and Short Walk to Nantucket Sound
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming three bedroom cottage that has a wonderful feeling of being "at the Beach". Enjoy sitting on the deck which of ...
From $493 per night (USD)VRBO
- Click For Pricing
VRBO
Completely Renovated Cape Cottage w\/ Linens Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
From the moment you walk through the door, you will instantly feel at home here. The cottage is very clean and cozy, tas ...
Click For PricingVRBO
- Click For Pricing
VRBO
Incredible Views, Walk to beaches, Beautiful deck, chef's kitchen
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
If you are looking for a beautiful home close to the beach, with every amenity, you've found your vacation retreat. Enjo ...
Click For PricingVRBO
- From $532 per night (USD)
VRBO
Charming Chatham home near Forest Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
New listing! This is our former primary home that we renovated and decorated with love. Every room has comfortable high ...
From $532 per night (USD)VRBO
- Click For Pricing
VRBO
Reel Paradise: Heated Pool, 676-C
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
This property is professionally managed by Pretty Picky Properties Ryder's Cove Resort: Heated Pool Sleeps 14 in 6 bed ...
Click For PricingVRBO
- From $415 per night (USD)
VRBO
Robin's Nest - Dog Friendly Chatham 4 Bedroom
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This home is represented by Nauset Rental, a local vacation rental management company. Beautiful, spacious 4 bedroom, 2 ...
From $415 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Newly Renovated Chatham Contemporary, Private Pond Access: 1151-C
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This property is professionally managed by Pretty Picky Properties Newly Renovated Lakefront Chatham Contemporary, Priv ...
From $507 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Close to Hardings Beach & Private Access to Oyster River
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Comfy and cozy four bedroom home near Hardings Beach! This recently updated Cape cottage is filled with new furnishings, ...
From $275 per night (USD)VRBO
- Click For Pricing
VRBO
Stage Island Estate - *New Availability* Waterfront with Pool and Private Dock
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
This home is represented by Nauset Rental, a local vacation rental management company. Located on its own point within ...
Click For PricingVRBO
- From $379 per night (USD)
VRBO
Lovely Cape Cottage Home < 1 mile to the beach! Gigabit WIFI 1000Mbps
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Relax at this charming South Chatham coastal retreat! Situated just 0.8 miles to Forest Beach & close proximity to the C ...
From $379 per night (USD)VRBO
- From $663 per night (USD)
VRBO
Beautiful Chatham
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is located in the Ryder's Cove area of Chatham MA. The main house consist of 2 bedrooms on the upper leve ...
From $663 per night (USD)VRBO
- Click For Pricing
VRBO
3\/10's of a Mile to Pleasant Street Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful Updated Home with Lots of Living Space, Close to Pleasant Street Beach. This pristine 3 bedroom, 3 bath home ...
Click For PricingVRBO
- From $374 per night (USD)
Expedia
Close to Bike Path 1 Mile to Beaches!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: 16673 - Mayflower Retreat: Close to Bike Path 1 Mile to Beaches! The Space: A quick pedal from the Cape Cod Ra ...
From $374 per night (USD)Expedia
- From $572 per night (USD)
VRBO
5 Bedroom Chatham Charmer
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Located in the highly desirable town of Chatham, this five bedroom, three bath rental home will meet all your vacation n ...
From $572 per night (USD)VRBO
- From $876 per night (USD)
Expedia
Large Chatham Rental w\/ 5 Bedrooms w\/ 5 Private Bathrooms
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
This stunning rental home is a vacationer’s dream! Easy and close access to the ponds, bike trails, conservation area a ...
From $876 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Picture Perfect Hardings Beach Rental
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Located just .89 miles away from Harding's Beach this newly renovated 3 bedroom 2 bath home is perfectly set up for a sp ...
From $500 per night (USD)VRBO
- From $569 per night (USD)
VRBO
Perfectly Located 3 Bedroom Chatham Charmer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Location is everything! The perfectly appointed 3 bed, 2 full bath home is just 1.3 miles to Chatham Main Street, 1.3 Mi ...
From $569 per night (USD)VRBO
- From $536 per night (USD)
VRBO
Chatham Village Charmer. Walk to Beach and Town.: 031-CDR
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is professionally managed by Pretty Picky Properties Chatham Village Charmer. Walk to Beach and Town. Re ...
From $536 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Cape Cod Beach Vacation Home
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 6
Classic Cape Cod style home .2 miles from marsh and .5 miles walk to full service Harding beach offering endless activit ...
From $300 per night (USD)Expedia
- From $375 per night (USD)
VRBO
*NEW LISTING* Peace and Quiet Pond Front
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Watch the sunset Mill Pond. Surrounded by nature the tranquility is perfection. Just minutes to Chatham Light, Cockle Co ...
From $375 per night (USD)VRBO
- Click For Pricing
Expedia
Dog-friendly home near Forest Beach with deck, grill, washer\/dryer and yoga room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Stagecoach Dreams Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $1493 per night (USD)
VRBO
Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beach: 177-CC
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 15
This home is professionally managed by Pretty Picky Properties Choice in Chatham: Sleeps 15, Pool, Walk to Town or Beac ...
From $1493 per night (USD)VRBO
- From $3215 per night (USD)
Expedia
Stunning Chatham Luxury Property With Pool, Spa and Beach Access
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Located just .9 miles from the Chatham Bars Inn and 1.3 Miles from Main Street, this 6 bedroom 6 full bath new construct ...
From $3215 per night (USD)Expedia
- From $729 per night (USD)
VRBO
Fabulous Chatham Rental With Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Nestled in one of the most coveted areas of Cape Cod, 63 Morris Island Road offers everything a discerning tenant could ...
From $729 per night (USD)VRBO
- From $1322 per night (USD)
Expedia
Pool and Private Association Beach In Cannon Hill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
ALL JUNE/JULY/AUGUST 2024 STAYS BOOKED BEFORE 5/31/24 RECEIVE A 10% DISCOUNT OFF THE RENT! Tucked in the private Cannon ...
From $1322 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Lovely vacation home less than a mile from Chatham beaches!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Traditional Cape Cod home with a large, private yard with a deck, outdoor shower and hammock in a quiet Chatham neighbor ...
From $300 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Chatham pond access with view
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy our large back yard and private road that leads to the Pond behind the house, for fishing, non-motor boating, padd ...
From $550 per night (USD)Expedia
- From $447 per night (USD)
VRBO
Updated, Clean Chatham Home on Quiet Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Long-term rentals preferred…7 day minimum. Relax comfortably with the whole family in this quiet yet centrally located t ...
From $447 per night (USD)VRBO
- From $566 per night (USD)
VRBO
Chatham Bliss - Dog Friendly oasis with EV Charging
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our recently updated getaway in charming Chatham, MA! Our pet-friendly retreat is the perfect destination for ...
From $566 per night (USD)VRBO
- From $826 per night (USD)
VRBO
Gorgeous, Modern, Dog Friendly Chatham 4 Bedroom with Central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This home is represented by Nauset Rental, a local vacation rental management company. Gorgeous, modern beach house out ...
From $826 per night (USD)VRBO
- From $888 per night (USD)
Expedia
Waterfront Renovated Home with Pool and Dock: 560-C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Waterfront Renovated Home with Pool and Dock Sleeps 8 Rents Friday - Friday during peak season Pets Considered It's r ...
From $888 per night (USD)Expedia
- From $420 per night (USD)
VRBO
Chatham Getaway- Completely Renovated Cape Cottage w\/ Linens Included
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
*Contact us for information on long-term booking opportunities!* This home is represented by Nauset Rental, a local vac ...
From $420 per night (USD)VRBO
- From $1323 per night (USD)
VRBO
Renovated Luxury Chatham Home with Pool & Hot Tub: 935-C
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties Renovated Luxury Chatham Home with Pool & Hot Tub Ho ...
From $1323 per night (USD)VRBO
- Click For Pricing
VRBO
Exquisite Cottage - Minutes to Village Center and Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome! This cottage is just perfect - it's adorable, fully independent and recently renovated. The cottage is 660 squa ...
Click For PricingVRBO
- From $350 per night (USD)
Expedia
Chatham Beach Facing 2 Bedroom Condo With Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic Chatham location with private association beach only minutes to downtown! White sandy beaches, dining and sho ...
From $350 per night (USD)Expedia