
Pet-friendly holiday rentals in Chatham
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Chatham
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

★ 0.4mi Beach &Village ★Firepit & Fireplace★ Bikes
✅4 adult bikes / helmets / beach chairs ✅Woodburning FPL in LR w/65” ROKU TV ✅Located at end private cul-de-sac, 0.4mi to ocean beach & 1/2mi to Village ✅Steps to restaurants & Sundae School Ice-Cream ✅Enjoy the backyard w/plenty of seating, fire-pit, outdoor shower & hammock ✅Large eat-in kitchen w/Island ✅2 Queen BR’s downstairs & 2 twin + rollaway in loft plus 1/2 bath ✅Pet Fee $30/day ✅1200 Mbps FastWiFi ✅Washer/Dryer ✅ Full A/C ✅All linens included & beds made Locally managed

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.

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes
☆ Waterfront, located on private saltwater beach (with central location) ☆ Sauna (year-round) ☆ Cozy fireplace (electric) ☆ 3-season patio ☆ 1% donated to Cape nonprofits ☆ 2 Kayaks & 2 Paddle boards ☆ Outdoor fire pit & charcoal grill ☆ Ample workspace ☆ Dog Friendly ☆ Washer/dryer ☆ 2 King Beds with 50" TVs in bedrooms ☆ Outdoor shower (open May through fall) ☆ Beach chairs provided ☆ Linens, all towels provided ☆ 10min from bay or ocean beach ☆ 15min MV & Nantucket ferries
Cape Cod Classic Cottage Near Forest Beach
See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

Private Pond-side Cape Cod Home
Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

The Sea Captain's Carriage House
The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.

Cape Hideaway
Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

Cozy Waterfront Apartment, Private Beach Access
Charming living space with nautical decor invites you to unwind off the grid for a few days. There is a window seat for reading, small high top for morning coffee, and all the accessories for a relaxing day at the beach. A five minute drive into town for local shopping and dining. Many scenic trails for walking and biking. Make us your base as you explore Cape Cod’s beautiful shores!

Violet’s Place- king bed- pet friendly- hot tub!
Fully renovated Cape Cod bungalow, less than a mile to West Dennis beach, bass river, restaurants and convenience store! The interior is chic with all new walk-in shower, soaking tub, boho butchers block kitchen and a warm living space with king bed and flat screen TV. Enjoy the pedicured yard with grill, fire pit, and private open roof hot tub! Pet friendly!

Pebbles-romantic cottage for two!
Pebbles, our sun drenched romantic cottage, is on nearly an acre of complete privacy with convenient parking. One adorable king BR, queen pull-out sleeper sofa in the living room, gas fireplace heats entire cottage, cable TV, full internet. Full indoor bath and outside shower and tub--complete privacy. Full kitchen and eating area.

Forbes, a South Chatham cottage
This cozy, two bedroom cottage is nestled in a wooded neighborhood and has a full kitchen, living room, 2 air conditioned bedrooms, a full bath, cable TV, Internet, a screened-in porch, shaded yard, outdoor shower, and a gas grill. Cockle Cove beach is a short walk (3/4 mile) . Weekly summer rentals only, Saturday until Saturday.
Popular amenities for Chatham pet-friendly home rentals
Pet-friendly house rentals

* Walk to the beach - Swiss Beach House! *

Sunburst Cottage on Long Pond

Pet Friendly-Private Family House-Near Beaches

Thinking of Summer Already? - Book Now Summer '26

Chatham Beach Cottage

Close to Beach Renovated Dog Friendly Cape Cottage

Chatham cottage w/ laundry & AC! Walk to beach!

Modern Beach & Pond Getaway | Heart of Cape Cod
Pet-friendly home rentals with a pool

Harwich Haven: Pool & Fire Pit

5-bedroom Cape with a pool and yard games.

Harwich House: Private Pool, Game Room & Putt-Putt

Game Room- Movie Projector Room- Fire Pit

Historic 1 Bed/In Town/Best Location/Hot tub/deck

Family + Dog Retreat | Fenced Yard + Pool + Beach

Winslow Acres [heated] Pool Escape; pool May-Oct

Renovated ranch with pool access
Private, pet-friendly home rentals

2 bedroom apartment

The Sunshine Cottage - cozy cape house!

Lake charm

Cottage Getaway walk to beach

Beachfront Cottage w. Yard + Town Access

Happy Home in Harwich/Fenced backyard/Dog friendly

Spacious studio on lovely pond in Chatham

Updated 3BR Bayview Dog Friendly | Dock
When is the best time to visit Chatham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $383 SGD | $436 SGD | $378 SGD | $462 SGD | $495 SGD | $603 SGD | $828 SGD | $799 SGD | $513 SGD | $465 SGD | $455 SGD | $432 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 holiday rentals that are pet-friendly in Chatham

Total holiday rentals
Explore 190 holiday rentals in Chatham

Nightly prices starting at
Chatham holiday rentals start at $115 SGD per night before taxes and fees

Verified guest reviews
Over 6,190 verified reviews to help you choose

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

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wifi availability
190 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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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Onset Beach
- Coast Guard Beach
- New Silver Beach
- Pinehills Golf Club
- Sandy Neck Beach
- Cahoon Hollow Beach
- Nickerson State Park
- Lighthouse Beach
- Cape Cod Inflatable Park
- Popponesset Peninsula
- Saquish Beach
- Race Point Beach
- Nauset Beach
- Skaket Beach
- Sea Gull Beach
- Scusset Beach State Reservation
- Marconi Beach
- Sandwich Glass Museum




