Chatham Rentals
From $497 per night (USD)VRBO
Chatham Get a Way - Forest Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly listed, beautiful charming 2 bedroom, 1 bath chatham cottage. Located just 4/10 of a mile from Forest Beach and ...
From $497 per night (USD)VRBO
From $591 per night (USD)Expedia
Newly Updated Central AC Sunroom Great Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $591 per night (USD)Expedia
From $547 per night (USD)VRBO
Charming Chatham condo - Oyster Pond views, pool, tennis court and water access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy the Chatham breezes and take advantage of the best the Cape has to offer whether staying on the property or g ...
From $547 per night (USD)VRBO
From $467 per night (USD)Expedia
5 BR - Beautiful Property-Chatham in-Town & Oyster Beach Inlet
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Absolutely beautiful vacation home with upscale furnishings throughout! Giant wraparound porch complete with comfy furni ...
From $467 per night (USD)Expedia
From $637 per night (USD)VRBO
Hot Tub, Fenced Yard & Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: 16651 - Smooth Sailing: Hot Tub, Fenced Yard & Dog Friendly The Space: Keep it classy this summer and spend a ...
From $637 per night (USD)VRBO
From $245 per night (USD)Expedia
Fully Updated Home w\/ Great Outdoor Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 16648 - Quail Trail: Fully Updated Home w/ Great Outdoor Space! The Space: This beautifully updated house in S ...
From $245 per night (USD)Expedia
From $658 per night (USD)VRBO
Walk to the beach! The Salty Breeze sleeps 10; updated house, bikes, beach toys!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to The Salty Breeze! Come enjoy the perfect vacation spent in Chatham, one of the most desirable summertime dest ...
From $658 per night (USD)VRBO
From $505 per night (USD)Expedia
Spacious w\/ Large Outdoor Area Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16637 - The Driftwood: Spacious w/ Large Outdoor Area Fire Pit! The Space: Our beautifully decorated, spacious ...
From $505 per night (USD)Expedia
From $1683 per night (USD)VRBO
Families: Enjoy Harwich, Pool, Large Hot Tub & AC!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Families only please, if you are a group of friends, please reach out to us before booking. AC is new for 202 ...
From $1683 per night (USD)VRBO
From $172 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 $172 per night (USD)VRBO
From $325 per night (USD)VRBO
Beautiful home with entertainment - near golf courses & Pleasant Bay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Harwich House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $325 per night (USD)VRBO
From $732 per night (USD)Expedia
Modern Luxury in Chatham with Water Views: 875-C
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties June rates just reduced! Modern Luxury in Chatham wi ...
From $732 per night (USD)Expedia
From $353 per night (USD)VRBO
Chatham Village - Center - Main Street Center Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a fantastic - location right off main street in Chatham downtown area - 5 minute walk to Oyster Pond Ocean Inlet ...
From $353 per night (USD)VRBO
From $432 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 $432 per night (USD)VRBO
From $1647 per night (USD)VRBO
5 Star Waterfront in North Chatham with dock, fire pit, and beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Listed as a top vacation rental by Conde Nast Traveler in 2021, this spacious 5-bedroom waterfront home by Eastward Ho C ...
From $1647 per night (USD)VRBO
From $741 per night (USD)Expedia
Enjoy your own PRIVATE POOL in Chatham! (2252)
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This uniquely beautiful home located in historic Chatham comfortably sleeps 12 with 5 bedrooms, 2.5 baths, plus two outd ...
From $741 per night (USD)Expedia
From $272 per night (USD)VRBO
South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cottage is an affordable Chatham getaway destination for a couple or small family who want to experience Cape Cod. ...
From $272 per night (USD)VRBO
From $635 per night (USD)VRBO
Beautiful Historical Home, close to beach & bike path.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 3 bedroom historical property (1850) located 1/4 mile to Red River Beach. 1/4 mile to the Cape Cod bike trail, ...
From $635 per night (USD)VRBO
From $658 per night (USD)VRBO
Near Beach, bike trail, Central AC, WiFi, Private Neighborhood
- 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 $658 per night (USD)VRBO
From $425 per night (USD)VRBO
Stunning Water Views, Swim and Kayak in Tidal River, Walk to Beach, AC, Like New
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
The River House is a recently built, beautifully furnished home, with stunning views of an idyllic bird watcher’s tidal ...
From $425 per night (USD)VRBO
From $377 per night (USD)VRBO
Charming Walk to Beach Chatham-Bayview Beach House--Central A\/C; Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Every room in this year-round home has been totally renovated and redesigned just a few years ago. Bayview Cottage fe ...
From $377 per night (USD)VRBO
From $337 per night (USD)Expedia
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sea House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $337 per night (USD)Expedia
From $1374 per night (USD)VRBO
Chatham Loop\/Stage Neck\/5 Bed\/6 Bath
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
https://www.youtube.com/watch?v=aFmta3dZpX8 Welcome to Over The Moon located in the heart of Chatham's Gold Coast just ...
From $1374 per night (USD)VRBO
From $548 per night (USD)Expedia
Cape Cod Nest: A Spacious Home with Large Deck, & Beautiful Yard with Firepit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cape Cod Nest: A Spacious Home with Large Deck, & Beautiful Yard with Firepit The Cape has some of the most beautiful b ...
From $548 per night (USD)Expedia
From $534 per night (USD)VRBO
Unique opportunity just opened up - July 5-13. Oyster Pond close to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
STEPS FROM OYSTER POND, SHORT WALK TO TOWN AND CAPE LEAGUE BASEBALL GAMES! This truly is a unique beach house in an excl ...
From $534 per night (USD)VRBO
From $384 per night (USD)Expedia
Charming Beach House ~ Beautifully Updated & Immaculate. Walk to Sandy Beaches
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28 ...
From $384 per night (USD)Expedia
From $557 per night (USD)VRBO
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Cozy and quiet 3 bedroom, 2 bath Cape style home with an expansive, beautifully landscaped yard…the largest in the area. ...
From $557 per night (USD)VRBO
From $365 per night (USD)VRBO
Beautiful Retreat \/ Hot tub\/ Walk to Ridgevale Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lovely, sun-filled, completely renovated, 4 bedroom 2 full bath house located within walking distance to beautiful, kid- ...
From $365 per night (USD)VRBO
From $421 per night (USD)VRBO
Walk 2\/10 mile to Lighthouse Beach. 1\/4 mi to downtown Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location, Location, Location! Get away from it all in this charming Chatham Village bungalow which is a stones throw fr ...
From $421 per night (USD)VRBO
From $309 per night (USD)VRBO
Short Walk to Beach From Clean, Beautiful 3BR\/2BA Home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pretty, completely renovated 3BR home on quiet cul de sac, located w/in a 5-10 minute stroll to beautiful, family-friend ...
From $309 per night (USD)VRBO
From $333 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 $333 per night (USD)VRBO
From $727 per night (USD)VRBO
Aren't you thinking about summer right now? Warm days and cool nights available!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect for families, or several couples, this home has plenty of light and a wrap around deck with marsh and ocean view ...
From $727 per night (USD)VRBO
From $361 per night (USD)VRBO
CHATHAM - 275. per night Oct-May! 1\/3 mile TO SANDY BEACHES, SHOPS, DINING. A+
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 5
CHATHAM - WALK TO BEACHES!! $225. PN LATE AUTUMN, WINTER, SPRING. $620. PN SUMMER 2025 (JUNE 21 - SEPT 01.) ENJOY REDU ...
From $361 per night (USD)VRBO
From $1668 per night (USD)Expedia
Pool and Private Association Beach In Cannon Hill RPAM006
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Tucked in the private Cannon Hill Neighborhood, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large ...
From $1668 per night (USD)Expedia
From $2175 per night (USD)VRBO
Oyster Pond Waterfront - Chatham, Massachusetts
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Capture spectacular sunrises, seasonal fireworks, and everything in between via the unobstructed panoramic water and tow ...
From $2175 per night (USD)VRBO
From $1321 per night (USD)VRBO
Booking for 2025 now! WATERVIEWS! 4min drive to Hardings Beach!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
We loved seeing the different groups who came through our house this year. We had bachelorette parties, multi-generation ...
From $1321 per night (USD)VRBO
From $1792 per night (USD)VRBO
Breathtaking Harwich Retreat w\/ Heated Pool and Spa RPAM086
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Prepare to be amazed as you pull into this stunning, fully renovated Gothic Revival manor with 1.2 acres of manicured gr ...
From $1792 per night (USD)VRBO
From $587 per night (USD)VRBO
Beautiful Harwich home with private pool in great location!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
You will fall in love with this tastefully furnished home located in a quiet neighborhood. This fantastic 2500+ sq/ft ...
From $587 per night (USD)VRBO
From $1954 per night (USD)VRBO
Elevate Your Cape Stay: Chatham Luxury with Pool & Beach RPAM026
- 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 luxury home s ...
From $1954 per night (USD)VRBO
From $1134 per night (USD)Expedia
Supremely Located Chatham Rental With Path To Private Beach RPAM054
- 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 $1134 per night (USD)Expedia
From $662 per night (USD)VRBO
Walk to The Monomoy Wildlife Sanctuary. Great space for relaxing and entertaining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spend your vacation by the beach! Charming 3 bedroom, 2 bath that can sleep 6 with 1 double bed, 2 twins, and a king in ...
From $662 per night (USD)VRBO
From $629 per night (USD)VRBO
NEW LISTING! Perfect family home, short walk to Chatham!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This completely renovated and newly painted home is located on a private road and just a few minutes walk away from all ...
From $629 per night (USD)VRBO
Click For PricingVRBO
Chatham Ocean View Home, Beach Accesso, 3 Decks, Pets Considered, Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our beautiful Cape Cod beach house is perfect for a relaxing vacation with family or friends. Nantucket Sound views and ...
Click For PricingVRBO
From $836 per night (USD)VRBO
Recently Remodeled 4 bedroom-sleeps-10 with A\/C-just one mile to the beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Recently Remodeled 4 bedroom-sleeps-10 with A/C-just one mile to the beach! This recently-remodeled 4 bedroom, 3.5 bath ...
From $836 per night (USD)VRBO
From $398 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 $398 per night (USD)VRBO
From $388 per night (USD)VRBO
Centrally Located Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Classic Cape Cod style home .2 miles from marsh and .5 miles walk to full service Harding beach offering endless activit ...
From $388 per night (USD)VRBO
From $349 per night (USD)VRBO
NEW LISTING Peace and Quiet Pond Front
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Watch the sunset Mill Pond. Surrounded by nature the tranquility is perfection. Just minutes to Chatham Light, Cockle Co ...
From $349 per night (USD)VRBO
From $659 per night (USD)Expedia
Pristine Chatham home walkable to town, CBI, Fish Pier and baseball field
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Chatham retreat CLOSE to EVERYTHING, walk to CBI, fish pier, town, baseball field etc. Completely remodeled to perfectio ...
From $659 per night (USD)Expedia
From $725 per night (USD)VRBO
Sprawling Home With Great Outdoor Space (2288)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
If you are looking for the perfect getaway to pamper your guests on your next Cape Cod vacation offering easy access to ...
From $725 per night (USD)VRBO
From $503 per night (USD)Expedia
House with central air on Chatham\/Harwich line - great for large groups!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
This spacious home is located right on the Chatham/ Harwich line allowing you to enjoy all that both towns have to offer ...
From $503 per night (USD)Expedia
From $1714 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 $1714 per night (USD)VRBO
From $877 per night (USD)Expedia
Heated Pool AC 1\/2 Mile to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 20
Summary: 17739 - Deja Blue: Heated Pool AC 1/2 Mile to Beach! The Space: Accommodations for twenty people, a heated poo ...
From $877 per night (USD)Expedia
From $752 per night (USD)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 ...
From $752 per night (USD)VRBO
From $485 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 $485 per night (USD)Expedia
From $253 per night (USD)VRBO
Updated Beach House Deck Outdoor Shower!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 16670 - A Touch of Blue: Updated Beach House Deck Outdoor Shower! The Space: Nautical colors and floods of nat ...
From $253 per night (USD)VRBO
From $518 per night (USD)Expedia
Spacious, Private Yard w Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: 17735 - Hawksnest: Spacious, Private Yard w Hot Tub! The Space: Escape to the serene shores of Harwich and dis ...
From $518 per night (USD)Expedia
From $543 per night (USD)VRBO
5 Min Walk to Red River Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 17740 - Absolute Beach: 5 Min Walk to Red River Beach! The Space: Happiness in Harwich is hard to hide from. A ...
From $543 per night (USD)VRBO
From $850 per night (USD)Expedia
5 Bedroom Chatham Charmer RPAM012
- 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 $850 per night (USD)Expedia
From $1208 per night (USD)VRBO
Large Chatham Rental w\/ 5 Bedrooms w\/ 5 Private Bathrooms RPAM007
- 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 $1208 per night (USD)VRBO
Click For PricingExpedia
Picture Perfect Hardings Beach Rental RPAM025
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 ...
Click For PricingExpedia
From $472 per night (USD)VRBO
Large, 3 Bedroom Private Home in East Harwich
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Newly renovated ranch home has plenty of room for both groups and individual guests to enjoy. It is ideally located near ...
From $472 per night (USD)VRBO
Click For PricingExpedia
Alluring, Upscale in Chatham, Striking Water View, Separate Guest House: 081-C
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
This property is professionally managed by Pretty Picky Properties. Alluring, Upscale in Chatham, Striking Water View, ...
Click For PricingExpedia
From $351 per night (USD)VRBO
Large Home w\/ Fire Pit and Dogs Welcome!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16674 - Heatherwood Haven: Large Home w/ Fire Pit and Dogs Welcome! The Space: Escape to Chatham, where baysid ...
From $351 per night (USD)VRBO
From $1071 per night (USD)Expedia
Beautiful 3 bedroom Cape with spacious deck and hot tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Lovely modern 3 bedroom home, located on a quiet cul-de-sac is the perfect place for a family vacation. Hop on the bike ...
From $1071 per night (USD)Expedia
From $1159 per night (USD)VRBO
On the water with amazing views! Dogs welcome! RPMS014
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Michelle Sylvia rental home. Comfort and charm abound in this updated 18th Century seaside farmhouse (four bedrooms and ...
From $1159 per night (USD)VRBO
Click For PricingExpedia
The Great Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private setting on quiet street on the outskirts of Chatham. Walk to beaches, bike path, local restaurants, short drive ...
Click For PricingExpedia
From $1130 per night (USD)VRBO
Luxury condo with all amenities. Pool tennis RPMS120
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in th ...
From $1130 per night (USD)VRBO
From $1462 per night (USD)Expedia
Luxury condo with pool, tennis and waterviews! RPMS118
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond. Beaut ...
From $1462 per night (USD)Expedia
From $1024 per night (USD)VRBO
Luxury condo in Chatham with amenities! RPMS119
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Michelle Sylvia high end collection. This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the ...
From $1024 per night (USD)VRBO
From $1876 per night (USD)Expedia
Chatham Resort Style Quality with Heated Pool, Close to Everything: 364-C
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 16
This property is professionally managed by Pretty Picky Properties Chatham Resort Style Quality with Heated Pool, Close ...
From $1876 per night (USD)Expedia
Click For PricingVRBO
Sunny, Cape-style home with a game room, yard, firepit, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Chatham Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For PricingVRBO
From $408 per night (USD)Expedia
Direct Private Beach Access (2290)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the perfect blend of luxury and convenience in this beautiful 2-bedroom, 2-bath waterfront townhouse that offer ...
From $408 per night (USD)Expedia
From $491 per night (USD)VRBO
Spacious w\/ Beautiful Yard & Dogs Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 17742 - A Wave From It All: Spacious w/ Beautiful Yard & Dogs Welcome! The Space: The Lower Cape boasts some o ...
From $491 per night (USD)VRBO
From $432 per night (USD)VRBO
Short Walk to Beautiful Ridgevale Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet, family neighborhood, a short stroll to the beach. 2 bedroom, 1 bath, outdoor shower, large deck to enjoy your mor ...
From $432 per night (USD)VRBO
From $352 per night (USD)VRBO
Updated, family-friendly, close to downtown Chatham & beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Renovated year round 3+ bedroom house with bonus office/bunk room with central AC, walking distance to downtown Chatham. ...
From $352 per night (USD)VRBO
From $341 per night (USD)Expedia
Friendly retreat with a deck, AC, and board games - stellar central location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Corner Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $341 per night (USD)Expedia
From $277 per night (USD)VRBO
Townhouse-style condo at The Hammond House located across from Lighthouse Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lighthouse Beach area! Townhouse-style condo at The Hammond House is located right across from Lighthouse Beach. Spend y ...
From $277 per night (USD)VRBO
From $795 per night (USD)Expedia
Pet friendly home with large backyard!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Enjoy your Chatham vacation at this spacious, 5 bedroom, 2 bath home. Offering 2 queens, a bunk bed and 4 twins, and a t ...
From $795 per night (USD)Expedia
From $1556 per night (USD)VRBO
Great Cockle Cove Home!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Family Retreat Destination! Let this 7 bedroom, 5 1/2 bathroom home serve as your luxurious home base for a multi-gener ...
From $1556 per night (USD)VRBO
From $773 per night (USD)VRBO
LOCATION & VIEW - Water Front Home In Chatham Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully renovated cottage on little mill pond. Renovation completed may 2016. A 4 minute walk to town of chatham. 3 bedroo ...
From $773 per night (USD)VRBO
From $885 per night (USD)VRBO
The Barn at Hardings Beach
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy ...
From $885 per night (USD)VRBO
From $406 per night (USD)Expedia
Gorgeous Home with Game Room Dog Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: 16675 - Summer Stunner: Gorgeous Home with Game Room Dog Welcome! The Space: Another Cape Cod vacation means a ...
From $406 per night (USD)Expedia
From $499 per night (USD)VRBO
Chatham Seascape
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This home is represented by Nauset Rental, a local vacation rental management company. The perfect vacation destinatio ...
From $499 per night (USD)VRBO
From $572 per night (USD)Expedia
New Listing - Oyster Bay Lookout - Near Downtown Chatham, Private Beach Access
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This home is represented by Nauset Rental, a local vacation rental management company. Introducing this charming Chath ...
From $572 per night (USD)Expedia
From $556 per night (USD)VRBO
Newly Built-3 Levels of Living, Central AC, Proximity to Beach and Marsh Views from Every Room!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom - 3.5 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $556 per night (USD)VRBO
From $380 per night (USD)Expedia
Steps to Private Association Beach. End Unit Condo at Outermost Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Updated Condo at Outermost Harbor. Enjoy amazing views of the famous Chatham sandbars or catch a glimpse of playful seal ...
From $380 per night (USD)Expedia
From $605 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 $605 per night (USD)VRBO
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Awesome Location! Right on the Chatham \"Loop\", Perfect for Long Walks!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Awesome Location! Right on the Chatham "Loop", it is Perfect for Long Walks! This 4-bedroom Cape House is close to town ...
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From $3193 per night (USD)VRBO
Spacious Custom Chatham Home w\/Pool, Guest Cottage & Water Views: 051-C
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
This property is professionally managed by Pretty Picky Properties. Spacious Custom Chatham Home w/Pool, Guest Cottage ...
From $3193 per night (USD)VRBO
From $1011 per night (USD)Expedia
Sprawling 5 BR Chatham Escape \/ Endless Outdoor Living & Entertaining Choices
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Completely renovated in 2017, this classic Cape is the perfect Chatham beach house. Offering an open flow layout with fi ...
From $1011 per night (USD)Expedia
From $478 per night (USD)VRBO
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 $478 per night (USD)VRBO
From $1539 per night (USD)Expedia
Prime Chatham Retreat with Pool, Spa & Style RPAM093
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your luxurious vacation rental in the exclusive enclave of Chatham, MA! This stunning homes boasts four spaci ...
From $1539 per night (USD)Expedia
From $1216 per night (USD)VRBO
Sunny Waterfront Home Perfect for Cape Cod Getaway!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Soak up the sun while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or ...
From $1216 per night (USD)VRBO
From $712 per night (USD)Expedia
Short stroll to Lighthouse Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Highly sought-after Bridge Street vacation rental! Enjoy your summer holiday in this beautiful home where Lighthouse Bea ...
From $712 per night (USD)Expedia
From $429 per night (USD)VRBO
0.6 Miles to Beach Great for families!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16677 - Nautical Nest: 0.6 Miles to Beach Great for families! The Space: Seals swim off shore while you soak u ...
From $429 per night (USD)VRBO
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Gorgeous distant views of Oyster Pond and Oyster River from the large second story deck.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Sea la Vie! This beautiful, spacious, well-appointed home has lots of extra living space and all the right a ...
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From $550 per night (USD)VRBO
Game Room Rooftop Deck Fire Pit!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: 16678 - Jawsome Getaway: Game Room Rooftop Deck Fire Pit!! The Space: Chatham is the hub of entertainment and ...
From $550 per night (USD)VRBO
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Close to Ridgevale Beach with great outdoor space!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Close to Ridgevale Beach! This spacious 4 bedroom, 3 bath vacation home is well maintained and just under a mile to popu ...
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Click For PricingVRBO
This charming rental on Stage Neck offers tons of privacy and outdoor space!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This charming rental on Stage Neck offers tons of privacy and outdoor space for easy entertaining. Relax on the back dec ...
Click For PricingVRBO
From $858 per night (USD)VRBO
Beautiful Chatham home...3 minute walk to salt water ocean beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Great location, spacious home and yard, private deck with brand new gas grill and comfy furniture. Beautifully decorated ...
From $858 per night (USD)VRBO