
House holiday rentals in Chatham
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Top-rated house rentals in Chatham
Guests agree: these houses are highly rated for location, cleanliness and more.

Lg Modern beach& Wychmere, AC, fast WIFI, king bed
Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

Cute cottage - walking distance to Ridgevale Beach
Retreat to this very quiet and peaceful residential shore neighbored on a dead end street. If LOCATION is what you're looking for, look no further! This year round cottage will serve as a comfortable and relaxing home away from home for your vacation, with walking rights to Ridgevale Beach about 300 yards from the front door. Provided in your home away from home vacation house are linens, towels, fully equipped kitchen, spacious out door shower, 2 roomy bedrooms, & 4 season porch to relax on.

Cottage with private beach in Hyannis Port
Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!

Stunning Home in Harwich Port
Welcome to our stunning retreat in charming Harwich Port! This beautiful 4-bed, 2-bath home is the perfect destination for your next getaway. The spacious interior and finished basement are perfect for families or groups and the big fenced-in yard is ideal for outdoor activities, relaxation and pets (please include pets when booking)! A 5 min drive from the beach and downtown, you'll enjoy all that the area has to offer. Book today and experience the best of Cape Cod in this beautiful home!

Slate House - a modern waterfront getaway
Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Beachfront Charmer! Newly Renovated.
Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

Lakefront House/Private Dock/Year Round Hot Tub/AC
Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

The Osprey Nest - Beach house with stunning views
The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

Cape Cod Cotuit Cottage, 3 Bed Near Beaches
5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!

Quaint Downtown Chatham Home
This charming and totally renovated Chatham home is on a private road in a downtown neighborhood of exclusive homes. Its ideal location enables you to walk to Lighthouse Beach about (1/2 mile) and 1 block from downtown Chatham. Also, the house is a quick walk to Children's Beach (Oyster Pond).

Close to everything in Chatham
4 bedrooms ( 1 King bed, 3 Queen beds, 2 Twin beds and a Queen sofa sleeper), 2 1/2 baths, sleeps 10, 3 levels of living space, yard and patio, deck bbq, lounge chairs, large patio table with umbrella, outdoor shower and washer and dryer.

cape cod riverview cottage
This is a 8 year old gambrel style custom Cape Cod shingled guest cottage is surrounded by lush landscaping and a beautiful view of a tidal river. The river leads to the ocean and is available for canoeing, sailing and kayaking.
Popular amenities for house rentals in Chatham
House rentals with a pool

Heated Pool, Game Room, Projector Room, Private

Harwich Haven: Pool & Fire Pit

Hot Tub, Game Room, near mayflower beach

Stunning Cape Home - Inground Pool, 5 Min To Beach

"Cape Escape" luxury home w/pool & beach access.

Modern Cape, Private Heated Pool, Beach, Golf

Spectacular beach & pool combo; beautiful sunsets!

Historic 1 Bed/In Town/Best Location/Hot tub/deck
Weekly house rentals

Ocean Front Townhouse

Spacious Cape Escape Near Rail Trail & Downtown

Sunburst Cottage on Long Pond

Relax and unwind from holidays at Red Door Retreat

Welcome to Daddy's Mink!

Lake Shore Cottage - Waterfront with Beach Access

Ocean view home on Cape Cod Bay

Charming Old Village Cape
Private house rentals

Charming Cape Cod Retreat–Walk to Long Pond Beach!

Amazing Location! Chatham Center, Walk to Beach!

Stunning Cape Cod Escape

Modern, Newly Renovated, 3-bed Peach Tree House

Stunning Cape cod home on Great Marsh

Sauna I Walk2Beach I Pet Friendly I Fire Pit

Chatham Family Vacation

“Rooster Cottage and Gardens” Entire Private Home
When is the best time to visit Chatham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $472 SGD | $463 SGD | $427 SGD | $463 SGD | $514 SGD | $637 SGD | $812 SGD | $784 SGD | $550 SGD | $463 SGD | $496 SGD | $511 SGD |
| Avg. temp | 0°C | 0°C | 3°C | 7°C | 12°C | 17°C | 21°C | 21°C | 18°C | 13°C | 8°C | 3°C |
Quick stats about house rentals in Chatham

Total holiday rentals
Explore 450 holiday rentals in Chatham

Nightly prices starting at
Chatham holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 12,110 verified reviews to help you choose

Family-friendly holiday rentals
430 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 170 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
440 of Chatham holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chatham rentals

4.9 Average rating
Chatham stays are highly rated by guests – averaging 4.9 out of 5!
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- Family-friendly rentals Chatham
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- Rentals with a hot tub Chatham
- Rentals with lake access Chatham
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- Luxury rentals Chatham
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- White Horse Beach
- Coast Guard Beach
- Pinehills Golf Club
- Chapin Memorial Beach
- Inman Road Beach
- Nauset Beach
- Lighthouse Beach
- Town Neck Beach
- Ellis Landing Beach
- Linnell Landing Beach
- New Silver Beach
- Nickerson State Park
- Falmouth Beach
- Cape Cod Inflatable Park
- Scusset Beach
- Forest Beach
- Cahoon Hollow Beach




