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From $881 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 $881 per night (USD)
VRBO
From $857 per night (USD)
Expedia
NEW Water View! Exceptional 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 $857 per night (USD)
Expedia
From $662 per night (USD)
VRBO
Stunning Waterfront Property Overlooking Pleasant Bay (2327)
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful rental home offers a serene and picturesque setting with marsh front views, water access just feet away, ...
From $662 per night (USD)
VRBO
From $556 per night (USD)
Expedia
Dogs welcome, huge yard right next to Rail Trail!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Summary: 17745 - Happy Tails: Dogs welcome, huge yard right next to Rail Trail! The Space: Discover Coastal Elegance in ...
From $556 per night (USD)
Expedia
From $806 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 $806 per night (USD)
VRBO
From $1109 per night (USD)
Expedia
Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friend
Bedrooms:
5
Bathrooms:
3
Sleeps:
8
Summary: 16680 - Seaside Sapphire: Elegant Chatham Home, steps to private association on Hardings Beach, Dog Friendly! ...
From $1109 per night (USD)
Expedia
From $589 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 $589 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Movie Theater Room, Direct Access to Bike Trail!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: 16681 - Summer On: Movie Theater Room, Direct Access to Bike Trail! The Space: Escape to this charming Chatham ...
From $305 per night (USD)
Expedia
From $275 per night (USD)
VRBO
Walk to Private Beach on Buck's Pond!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: 17721 - Float On: Walk to Private Beach on Buck's Pond! The Space: Welcome to your dream vacation home nestled ...
From $275 per night (USD)
VRBO
From $646 per night (USD)
Expedia
Waterfront home with lovely lake views, great deck, sun porch & fireplace
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Mill Pond Vista Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $646 per night (USD)
Expedia
From $368 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 $368 per night (USD)
VRBO
$Amazing Family Home w\/a separate extra Cottage and Game Barn!$
From $788 per night (USD)
Expedia
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 $788 per night (USD)
Expedia
From $1115 per night (USD)
VRBO
Chatham Vacation Rental With Pool and Charm to Spare! RPAM096
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 $1115 per night (USD)
VRBO
$Secluded North Chatham Cottage for Entire Summer [July\/August]!$
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
$Chatham Getaway w\/ Trail Access, 2 Mi to Beaches!$
From $415 per night (USD)
VRBO
Chatham Getaway w\/ Trail Access, 2 Mi to Beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Your next Cape Cod adventure awaits at this cozy Chatham vacation rental. Perfect for a memorable family getaway on the ...
From $415 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Explore Downtown and Pleasant Bay!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: 18836 - Sunny Escape: Explore Downtown and Pleasant Bay! The Space: Your Brewster vacation awaits, in this id ...
From $373 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Affordable Family Getaway Sleeps 7, Near Bike Path, Beach, Golf, Harwich Center
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Cape-style home in a family-friendly neighborhood. Open floor plan with large living room and dining room (seating for 6 ...
From $407 per night (USD)
VRBO
From $1918 per night (USD)
VRBO
Water views, private beach and spectacular sunsets from highest point in town.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This large, beautiful home is the perfect place to stay for your next beach vacation: whether you’re hosting a big group ...
From $1918 per night (USD)
VRBO
From $1880 per night (USD)
VRBO
Walk to beach, ball fields, Chatham Bars Inn and town from this central location
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This large, newly renovated home is the perfect spot for your Chatham getaway. It sits on a beautifully landscaped lot w ...
From $1880 per night (USD)
VRBO
From $1880 per night (USD)
VRBO
Large, beautiful home with extraordinary design features and bonus rooms galore
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This large, gorgeous home is perfect for entertaining, set on an acre of land with a private yard and large patio. The h ...
From $1880 per night (USD)
VRBO
From $554 per night (USD)
VRBO
Sandy Feet Retreat: 040-C Updated home on large lot near Hardings Beach in S. Chatham
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This property is professionally managed by Pretty Picky Properties. Updated Home, 1.5 Miles to Hardings Beach, 5 Min Dr ...
From $554 per night (USD)
VRBO
From $361 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 $361 per night (USD)
VRBO
From $886 per night (USD)
VRBO
Fido friendly Walk to Red River Beach - Sleeps 20 - Hot tub - Bring your boat!
Bedrooms:
5
Bathrooms:
8
Sleeps:
14
Come and relax with your dog in our private, spacious and newly remodeled 8 bedroom (12 beds - 1 king, 1 double, one fu ...
From $886 per night (USD)
VRBO
$Panoramic Water Views w\/ Private Beach!$
From $1781 per night (USD)
Expedia
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 $1781 per night (USD)
Expedia
From $491 per night (USD)
VRBO
3 bed, 2 bath, dog-friendly, central AC, Wifi sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Bathrooms - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. M ...
From $491 per night (USD)
VRBO
$Chatham Home w\/ Spacious Deck: 2 Mi to Beaches!$
From $414 per night (USD)
Expedia
Chatham Home w\/ Spacious Deck: 2 Mi to Beaches!
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
Experience beachside bliss in Cape Cod when you stay at this 4-bedroom, 3-bath South Chatham vacation rental! This home ...
From $414 per night (USD)
Expedia
From $381 per night (USD)
VRBO
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 $381 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Charming home with access to CC Rail Trail!
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 $474 per night (USD)
Expedia
From $441 per night (USD)
VRBO
Charming Cape Cod home, central to everything! Pet-friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming Cape Cod home is central to all of the Cape. Our three bedroom, two bath home (+ outdoor shower!) is a gre ...
From $441 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 Pricing
Expedia
From $1076 per night (USD)
VRBO
Family & Dog friendly Chatham house with tennis &water access
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
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 $1076 per night (USD)
VRBO
From $1076 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. Escape with your family and friends t ...
From $1076 per night (USD)
VRBO
From $1024 per night (USD)
VRBO
Wonderful dog-friendly rental close to downtown Chatham and Oyster Pond Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wonderful dog friendly rental for the whole family, with access path to a private beach deeded at White's Pond! Close to ...
From $1024 per night (USD)
VRBO
From $733 per night (USD)
Expedia
Water Views Over Bucks Creek & Nantucket Sound
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Stay at this idyllic 3 bedroom 3 bath Hardings Beach Hills home with water views and steps to the association dock on ...
From $733 per night (USD)
Expedia
From $1002 per night (USD)
VRBO
Pet friendly home with beautiful views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Pet Friendly with beautiful views!! Bright open living, dining area has a large slider right onto the back deck with wat ...
From $1002 per night (USD)
VRBO
$Stroll to Chatham's Popular Shops & Dining \/ Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound$
From $3929 per night (USD)
Expedia
Stroll to Chatham's Popular Shops & Dining \/ Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound
Bedrooms:
8
Bathrooms:
7
Sleeps:
16
Stroll to Chatham's Popular Shops & Dining / Or Walk to Andrew Hardings Beach from This NEW Impeccable Compound . Recent ...
From $3929 per night (USD)
Expedia
From $709 per night (USD)
VRBO
Newly Renovated Home in Chatham, Walk to Town and Beach: 016-C
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This property is professionally managed by Pretty Picky Properties. Newly Renovated Home in Chatham, Walk to Town and B ...
From $709 per night (USD)
VRBO
From $485 per night (USD)
VRBO
Chatham EsCAPE: At The Heart Of It All!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This charming 3-bedroom, 2-bathroom home is ideally situated between the tranquil Ridgevale Beach and the vibrant Chatha ...
From $485 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Close to Beach Renovated Dog Friendly Cape Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
4 minutes from the beach and nestled on a spacious half acre set back more than 250 feet on a private road, this newly r ...
From $425 per night (USD)
VRBO
From $2100 per night (USD)
Expedia
Exclusive Harwich Haven: Pool, Spa and More RPAM068
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Welcome to 8 Bascom Hollow, a truly luxurious Cape Cod escape. Located in East Harwich, this home offers tenants an exce ...
From $2100 per night (USD)
Expedia
From $790 per night (USD)
VRBO
Dog friendly, 4 bdrm, sleeps 10, game room, near beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
4 Bedroom - 2.5 Baths - Sleeps 11 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $790 per night (USD)
VRBO
$Two-story dog-friendly retreat with enclosed yard, playset, W\/D, & firepit$
From $343 per night (USD)
Expedia
Two-story dog-friendly retreat with enclosed yard, playset, W\/D, & firepit
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Sand Dollar Dreams Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $343 per night (USD)
Expedia
From $365 per night (USD)
VRBO
New! Chatham Cottage- 1 Mile to Downtown & Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Escape to our charming 2 bed/1 bath North Chatham cottage! A short walk to Chatham's best beaches and downtown shops an ...
From $365 per night (USD)
VRBO
From $653 per night (USD)
Expedia
3 bedroom, 2.5 bathroom, sleeps 10, half mile to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
4 Bedroom - 2.5 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $653 per night (USD)
Expedia
From $769 per night (USD)
VRBO
Harwichport Haven
Bedrooms:
6
Bathrooms:
4
Sleeps:
12
Nestled in the picturesque coastal town of Harwich Port, this charming retreat offers the perfect blend of comfort and s ...
From $769 per night (USD)
VRBO
Click For Pricing
Expedia
Steps to Chatham's Historic Downtown
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Luxury Retreat on Popular Main Street Chatham. This unique hide-a-way is a spacious 2 bedroom 2nd floor condo in the he ...
Click For Pricing
Expedia
From $602 per night (USD)
VRBO
Steps to Chatham's Historic Downtown
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury Retreat on Popular Main Street Chatham. This unique hide-a-way is a spacious 2 bedroom 2nd floor condo in the he ...
From $602 per night (USD)
VRBO
From $2091 per night (USD)
Expedia
Beautiful 5 BR property with pool and hot tub!
Bedrooms:
5
Bathrooms:
3
Sleeps:
10
2024 Rental Rates: In-Season: $11,000 per week, Plus Fees and Taxes No Off-Season Click for More Photos, Map, and A ...
From $2091 per night (USD)
Expedia
From $625 per night (USD)
VRBO
Fantastically located Chatham house - New patio, refurbished
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Fantastically located Chatham house - New patio, refurbished ( PET FRIENDLY) Beautiful Family Home w/ fire pit and <1 ...
From $625 per night (USD)
VRBO
From $560 per night (USD)
Expedia
Stroll To Lighthouse Beach or Chatham's Charming Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
NEW LOWER PRICING! Best location to spend your days in Chatham! This comfortable condominium overlooks the peaceful m ...
From $560 per night (USD)
Expedia
From $1122 per night (USD)
VRBO
Waterfront Pet Friendly Home, with best views in Chatham!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Classic, Cape Cod home, sitting high above Oyster River and Stage Harbor Lighthouse... Views from every window! Plenty ...
From $1122 per night (USD)
VRBO
From $489 per night (USD)
Expedia
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 $489 per night (USD)
Expedia
$Newly Renovated and Ideally Located \/ Close to Chatham's Idyllic Downtown$
From $595 per night (USD)
Expedia
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 $595 per night (USD)
Expedia
From $689 per night (USD)
Expedia
BOATHOUSE on Pleasant Bay - swim, fish, kayak, etc. right off your front porch.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Like living on a yacht without the rocking - originally built to house boats, the Boathouse is cozy like a ship with wat ...
From $689 per night (USD)
Expedia
From $444 per night (USD)
VRBO
Charming Chatham Abode with Sunroom!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 16686 - Chatham Life: Charming Chatham Abode with Sunroom! The Space: Embark on a journey into the quintessent ...
From $444 per night (USD)
VRBO
From $646 per night (USD)
Expedia
Immaculate in South Harwich, Pool, Walk to Beach: 015-HD
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Immaculate in South Harwich, Brand New Pool, Close t ...
From $646 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $821 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 $821 per night (USD)
Expedia
From $3812 per night (USD)
VRBO
Stunning Beach Retreat Walk to Chatham Bars Inn, & Town
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
This amazing seven bedroom Chatham home is located just .5 miles from Chatham’s beautiful downtown shopping area. It is ...
From $3812 per night (USD)
VRBO
From $643 per night (USD)
VRBO
Walk to downtown Chatham!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your Chatham adventure begins at this lovely 3-bedroom house. With 2 queen beds and 1 full bed, it's the perfect retreat ...
From $643 per night (USD)
VRBO
From $697 per night (USD)
VRBO
Walk to Downtown Chatham, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 16688: Sand Bar - Walk to Downtown Chatham, Steps to Beach! The Space: Introducing Sand Bar: Your Private Have ...
From $697 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Waterfront Home With Dock and Two Water Facing Decks! (2372)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to your serene waterfront retreat on Taylors Pond, offering direct access to Cockle Cove and the vast expanse of ...
From $546 per night (USD)
Expedia
From $477 per night (USD)
VRBO
FRIDAY TO FRIDAY RENTAL.... Cozy beach house close to Hardings Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
FRIDAY TO FRIDAY RENTAL.... Cozy beach house sleeps 9 with 4 bedrooms (2 queen, double, 2 twins) and 2 baths, hardwood f ...
From $477 per night (USD)
VRBO
Click For Pricing
Expedia
Cottage on freshwater lake with short walk to town beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our three bedroom 1 bathroom cottage was completely renovated in 2019. A beautiful 4 acre private property with a short ...
Click For Pricing
Expedia
$Water-view house near golf with firepit, grill, deck, central AC & washer\/dryer$
From $423 per night (USD)
VRBO
Water-view house near golf with firepit, grill, deck, central AC & washer\/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Chatham Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $423 per night (USD)
VRBO
$Elegant Coastal Retreat In Chatham w\/ Private Association Beach RPAM067$
From $1881 per night (USD)
Expedia
Elegant Coastal Retreat In Chatham w\/ Private Association Beach RPAM067
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to your dream getaway in Chatham, Massachusetts: 49 Patterson Road. Nestled along the coastline in a lovely neig ...
From $1881 per night (USD)
Expedia
From $951 per night (USD)
VRBO
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Stunning 4-Bedroom Oasis in a great location with Pool, Hot tub, and outdoor kitchen.. Your comfort and enjoyment are ...
From $951 per night (USD)
VRBO
From $403 per night (USD)
Expedia
Stunning Marsh Views, Near Pleasant Street Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16689: Lady Slipper - Stunning Marsh Views, Near Pleasant St. Beach! The Space: Nestled in the serene enclave ...
From $403 per night (USD)
Expedia
From $629 per night (USD)
VRBO
Ridgevale Retreat: 027-C Updated Beach House near Ridgevale Beach
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This home is professionally managed by Pretty Picky Properties Updated Beach House near Ridgevale Beach Sleeps 6 2 Bed ...
From $629 per night (USD)
VRBO
From $765 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 $765 per night (USD)
Expedia
From $925 per night (USD)
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 ...
From $925 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Cozy Chatham Getaway- minutes to all things Cape Cod- New listing!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to your perfect beach getaway in beautiful Chatham! This charming four-bedroom, two-bathroom cottage is just 2 m ...
From $575 per night (USD)
Expedia
From $571 per night (USD)
VRBO
Brand New Four Bedroom Home Near Beach and Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Brand new 4 bedroom, 2 bath North Chatham home near town and beach. The property boasts a designer kitchen, luxury marbl ...
From $571 per night (USD)
VRBO
From $744 per night (USD)
Expedia
Chatham Cape Cod Retreat, near boat yards, Harding's Beach, Stage Harbor Light
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
This modern Chatham home, filled with books and art, and surrounded by nature, is a peaceful retreat for those who appre ...
From $744 per night (USD)
Expedia
From $1120 per night (USD)
VRBO
Private Beach, Beautiful Neighborhood, Well-Behaved Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
The perfect spot, offering lovely outdoor amenities such as a large, beautiful hedged yard for outdoor activities, a cov ...
From $1120 per night (USD)
VRBO
From $1055 per night (USD)
VRBO
Private Beach, Beautiful Location, Well-Behaved Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
This is a 5* "Exceptional" property but all its past reviews did not convey when it was recently relisted. Highwood Co ...
From $1055 per night (USD)
VRBO
Click For Pricing
VRBO
Amazing 4 Bedroom Home! Walk to Downtown Chatham and Oyster Pond!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Beautiful four bedroom home located just steps to all the signature shops and restaurants on Main Street! Leave your str ...
Click For Pricing
VRBO
$3 Bedroom Sea-Side Cottage w\/ Beach Access RPAM083$
From $1043 per night (USD)
Expedia
3 Bedroom Sea-Side Cottage w\/ Beach Access RPAM083
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled at the end of Little Beach Road in Chatham, this charming 3-bedroom, 2-bathroom cottage invites you to indulge i ...
From $1043 per night (USD)
Expedia
$2 Bedroom Sea-Side Cottage w\/ Beach Access RPAM085$
From $778 per night (USD)
VRBO
2 Bedroom Sea-Side Cottage w\/ Beach Access RPAM085
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled at the end of Little Beach Road in Chatham, this charming 2-bedroom, 1-bathroom cottage invites you to indulge i ...
From $778 per night (USD)
VRBO
$Charming house with patio, Washer\/Dryer, & central location$
From $724 per night (USD)
Expedia
Charming house with patio, Washer\/Dryer, & central location
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Dreamcatcher Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $724 per night (USD)
Expedia
$Beautiful Chatham, Sun Sand & Surf. 8\/10 mile to beaches ,pet friendly home$
From $572 per night (USD)
VRBO
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 $572 per night (USD)
VRBO
$New Home, Dogs ok. A\/C, near beach, shopping$
From $1243 per night (USD)
Expedia
New Home, Dogs ok. A\/C, near beach, shopping
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
3 Bedroom - 3.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $1243 per night (USD)
Expedia
From $637 per night (USD)
VRBO
18 Bearberry Lane South Chatham - Rhododendron Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $637 per night (USD)
VRBO
$Downtown Chatham Luxurious & Spacious Condo w\/ Roof Deck - Close to Oyster Pond$
From $659 per night (USD)
VRBO
Downtown Chatham Luxurious & Spacious Condo w\/ Roof Deck - Close to Oyster Pond
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is ...
From $659 per night (USD)
VRBO
From $438 per night (USD)
VRBO
2 bd, 2bth dog-friendly cottage on conservation land
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
2 Bedroom - 2 Baths - Sleeps 5 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $438 per night (USD)
VRBO
From $348 per night (USD)
Expedia
Cape Cod Cottage Near Beaches & Bike Trail
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Summary: Welcome to Harwich—your ideal Cape Cod getaway. This delightful home sleeps 6 and features 4 bedrooms: 2 with q ...
From $348 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Wifi, AC, 4 bedrooms, 3 bathrooms, additional sleep space and bonus living room in the lower level
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
3 Bedroom - 3 Bath - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $570 per night (USD)
VRBO
From $1286 per night (USD)
Expedia
New build! Walk to beach, lots of room, great outdoor space, dogs ok
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
4 Bedroom - 3 Baths - Sleeps 10 Complimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish to ...
From $1286 per night (USD)
Expedia
From $621 per night (USD)
VRBO
Chatham Shenanigans, Chatham Shenanigans
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Experience the beauty of Cape Cod at Chatham Shenanigans. This beautiful, well-appointed, bright home is centrally locat ...
From $621 per night (USD)
VRBO
From $711 per night (USD)
Expedia
Walk to Hardings Beach and private association beach, newly refreshed
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom - 2 Baths - Sleeps 6 During peak summer weeks, our properties typically require a 7-night stay, either Friday- ...
From $711 per night (USD)
Expedia
From $589 per night (USD)
VRBO
3-bedroom house in charming Chatham with WiFi, fitness room, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 3-bedroom house in Chatham is perfect for your escape to relaxation. With 1 king bed, 1 queen bed, and 4 twin beds, ...
From $589 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Quiet South Chatham 2-Bedroom House, Close To Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Just listed well kept 2 bedroom Chatham home just a short drive from popular Rigdevale, Cockle Cove, and Hardings beache ...
From $399 per night (USD)
Expedia
From $1488 per night (USD)
VRBO
Waterfront, Updated 4 Bedroom Home with Views of Stage Harbor & Nantucket Sound
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Recently updated waterfront home overlooking Snake River, Stage Harbor & Nantucket Sound on Stage Island. 4+ bedroom, 3 ...
From $1488 per night (USD)
VRBO
From $1250 per night (USD)
VRBO
New 2025 Chatham Hideaway - Peaceful Woodland Overlooking Minister's Pond
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Welcome to Chatham Hideaway! This sprawling estate, surrounded by woodland and lush gardens, offers a private setting fo ...
From $1250 per night (USD)
VRBO
From $2678 per night (USD)
VRBO
Chatham Gem with Pool & High-End Style RPAM104
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
NEW FOR THE 2025 SEASON! Welcome to your perfect Cape Cod getaway in the heart of Chatham! This stunning 4-bedroom, 3.5- ...
From $2678 per night (USD)
VRBO
From $649 per night (USD)
Expedia
Secluded Quiet Family-Friendly Cape Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a secluded Cape Cod oasis we call the Hidden Hollow. This beautiful, family-friendly home is just a short driv ...
From $649 per night (USD)
Expedia
Click For Pricing
VRBO
Charming Guest House, with Waterviews & Private Beach! Perfect for Fun Weekends!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in South Orleans, this pet-friendly sun-filled Guest House offers 2 large bedrooms and 2 full baths. Located in ...
Click For Pricing
VRBO
From $411 per night (USD)
Expedia
Cozy Retreat in South Chatham (2374)
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our cozy single-family home located in beautiful South Chatham. This property features 3 comfortable bedrooms ...
From $411 per night (USD)
Expedia
From $764 per night (USD)
VRBO
Perfect beach house to spend your summer days in!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Picture this, a bright and airy 3 bedroom, 3 bath beach house, complete with two twin beds and two queen beds, awaits to ...
From $764 per night (USD)
VRBO
From $2526 per night (USD)
VRBO
Rambling 9 bedroom within walking distance to Red River Beach.
Bedrooms:
7
Bathrooms:
9
Sleeps:
14
Rambling 9 bedroom, updated home with layout flexibility (3 living rooms, 2 kitchens!). Perfect for families traveling t ...
From $2526 per night (USD)
VRBO

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