Pet-friendly vacation rentals in Chatham

4.83 out of 5 average rating, 509 reviews

The image displays four sections of the cottage. A cozy sleeping area features a full-size bed with soft linens. A bright kitchen with marble counters is visible, alongside a comfortable living space with seating. An outdoor deck with furniture showcases a partially fenced yard.

Tiny home in Dennis Port

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes

Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! ($25/nt) This 300sq.ft "TINY HOUSE" is 0.4 mi from the ocean beach & 1/2 mi from Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counters ✅ 2 Bike ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels-we do not provide linens ✅ Pet friendly-only 1 pet as the cottage is tiny $25/nt

4.86 out of 5 average rating, 425 reviews

The vintage beach cottage is depicted with a light blue exterior, settled near the edge of a sandy beach. Waves gently crash against the shoreline while a lush green area surrounds the cottage, providing a serene coastal setting. A single vehicle is parked near the entrance.

Cottage in East Sandwich

Bold Oceanfront Cottage w/Pvt Beach ~ Lil Sea Sass

RARE: DIRECT OCEANFRONT & BEACHFRONT CAPE COD COTTAGE — DOG FRIENDLY — LOCATED ON THE COTTAGE’S VERY OWN PRIVATE BEACH! Lil’ Sea Sass is a 3 BR vintage beach cottage that is nestled in the dunes offering unparalleled ocean views and is located in a very private serene setting. This oasis is near the end of a private road and then down a long drive — with free guaranteed parking for 2+ cars! Amenities include: gas fireplace, fire table, FAST WIFI, central AC & heat, and an outdoor shower.

4.98 out of 5 average rating, 205 reviews

A serene view of a crystal clear pond is framed by lush trees. The calm water reflects the blue sky and scattered clouds, creating a tranquil atmosphere. A wooden pathway leads to the water's edge, inviting exploration and relaxation.

Cottage in Dennis

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

4.95 out of 5 average rating, 295 reviews

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.

4.89 out of 5 average rating, 114 reviews

A well-maintained garden features colorful flowers, including red poppies and purple lavender, set against a stone retaining wall. The cottage, visible in the background, includes a vibrant orange awning and an American flag flying above, surrounded by lush greenery.

Home in South Yarmouth

Cheerful, renovated 2 bdrm-block to beach. Dog ok.

ARTIST and AUTHOR'S Cape Cottage! Dog Friendly-Freshly decorated Introductory Rates! Located .2 miles from the beaches in South Yarmouth. Be among the first to enjoy "My Two Cents" aka "Poppie's Place"- a quintessential, cheerfully remodeled home surrounded by hydrangeas, roses, and colorful perennials. Tucked off Seaview Avenue on a private lane you will enjoy easy access to several beaches, shops, Captain Parker's, Skipper’s and other great restaurants, Pirate's Cove mini golf, museums.

4.98 out of 5 average rating, 314 reviews

A cozy living space features a striped sofa and a round table set near a rug. Light from the windows brightens the room, which leads to a bedroom visible in the background, adorned with a patterned quilt and vibrant pillows.

Cottage in Pocasset

Upper Cape Cozy Cottage

Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.

5 out of 5 average rating, 332 reviews

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in West Yarmouth

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

4.93 out of 5 average rating, 186 reviews

A cozy cottage is framed by tall trees, showcasing a landscaped yard with a mix of grass and small shrubs. The home features a light-colored exterior with dark shutters and a welcoming front porch with steps leading up to the entrance.

Cottage in Chatham

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.

Superhost

The exterior view presents a two-story condo unit with a stairway leading to the entrance. Lush greenery surrounds the path, while well-maintained shrubs complement the soft landscaping. The balcony above offers additional outdoor space, enhancing the overall appeal of the building.

Condo in Brewster

4.88 out of 5 average rating, 297 reviews

Shining Sea Condo

Ocean Edge Condo with cathedral ceilings! Beautiful private deck located on the 5th hole of the Ocean Edge golf course! Located within Eaton village. TWO KING beds, along with pullout couch allows 6 to sleep comfortably. Linens are included!! Large kitchen with washer/ dryer, AC units and heat throughout the entire unit. Wifi and THREE smart TVs with ROKU devices. Flexible dates allows guests to stay whatever length they would like instead of a mandatory week. Come enjoy!

4.98 out of 5 average rating, 330 reviews

A spacious living room features modern furnishings arranged for comfort. A large flat-screen TV is mounted above an electric fireplace. Natural light enters through multiple windows, and a playful dog portrait decorates the wall. A patterned rug anchors the seating area.

Home in Falmouth

The Driftwood Home, 5 min from Mashpee Commons, AC

- NOW PET FRIENDLY! - 15 min to Old Silver, South Cape, and Falmouth Heights beaches - 5 min to Mashpee Commons - 15 min to Falmouth Main St - 1600 square feet, built in 2014, w/ central AC - Large kitchen w/ all cookware and utensils - Outdoor deck with seating, fire pit, and grill - 55” Smart TV - 10 min to Shining Sea Bike Trail - Less than 10 min to Falmouth, Cape Cod, and Quashnet Valley Country Clubs - Centrally located to all of the Upper Cape - No parties or events!

Guest suite in West Falmouth

A cozy living area features a comfortable gray sofa with decorative pillows and a wooden coffee table. Natural light fills the space, highlighting a dining table with four chairs. A doorway leads to the kitchen, while a wall-mounted TV provides entertainment options.

4.99 out of 5 average rating, 191 reviews

The Sea-Cret Garden, Guest Apartment

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

5 out of 5 average rating, 195 reviews

An outdoor patio area is illuminated softly at dusk, featuring a dining set with a table and several chairs arranged on a patterned rug. Lush greenery and flowering plants surround the space, while lanterns provide a gentle glow, enhancing the tranquil environment.

Home in Mashpee Neck

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!

Popular amenities for Chatham pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 53 reviews

A charming coastal home is presented in a scenic setting, featuring a light grey exterior and a welcoming front porch. Brick walkways lead to the entrance, flanked by well-maintained gardens and landscaped shrubs. A gravel driveway provides ample parking alongside the property.

Home in Pocasset

Coastal Retreat Near Saltwater Beaches & Boating

4.82 out of 5 average rating, 17 reviews

Home in West Harwich

The Sunshine Cottage - cozy cape house!

An inviting outdoor area features a fire pit surrounded by several blue Adirondack chairs on a pebble surface. A dining table is set nearby, framed by lush greenery and the soft touch of flowering plants in the foreground.

5 out of 5 average rating, 10 reviews

Spacious Cape Escape Near Rail Trail & Downtown

4.98 out of 5 average rating, 47 reviews

The exterior of the home is shown, featuring a well-manicured lawn with stone pathways leading to the entrance. Blue shutters frame the windows, and a bright red door adds a pop of color. The serene lake is visible beyond the property.

Home in Centerville

Lake charm

5 out of 5 average rating, 13 reviews

A cozy exterior view of the house features a gravel driveway leading up to a classic Cape Cod cottage. Lush green lawns are complemented by well-maintained gardens and tall trees. The house is set back from the street, with a spacious fenced-in yard enhancing privacy.

Home in Dennis Port

Cottage Oasis by Lake-Kayaks, Fire Pit & Huge Yard

5 out of 5 average rating, 68 reviews

A spacious house is set on a green lawn, with well-maintained shrubs and small trees in the front. The two-story structure features a welcoming porch, large windows, and a two-car garage. A driveway leads up to the entrance and is bordered by landscaping.

Home in Harwich

Dog and family friendly fun in Harwich

4.96 out of 5 average rating, 25 reviews

The exterior of a spacious single-story home is presented, featuring a blend of shingle and wood siding. A covered entryway is framed by greenery, while a stone pathway leads to the front door. Large windows reflect natural light, contributing to the inviting ambiance.

Home in Centerville

Sunny Cape Home, Bike to Beach, Central AC

5 out of 5 average rating, 72 reviews

A backyard space is equipped with a fire pit surrounded by four white Adirondack chairs, providing a cozy gathering area. String lights hang overhead, illuminating the outdoor dining table set for a meal. A charming cottage is visible in the background, enhancing the inviting atmosphere.

Home in West Dennis

Sunset Sabbatical Cape Cod

Pet-friendly home rentals with a pool

5 out of 5 average rating, 32 reviews

An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.

Home in Harwich Center

Harwich Haven: Pool & Fire Pit

4.91 out of 5 average rating, 33 reviews

The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.

Home in Orleans

5-bedroom Cape with a pool and yard games.

4.94 out of 5 average rating, 16 reviews

An outdoor area features a spacious table with four chairs under a large yellow umbrella, providing shade. Nearby, a private hot tub is tucked away among trees, while a small white side table and a blue adirondack chair complete the relaxing ambiance.

Home in Dennis Port

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

Superhost

A sunlit corner of the guesthouse features a dining area with a round table and four wooden chairs, surrounded by large windows that offer views of the ocean. A decorative cabinet and television are positioned nearby, enhancing the inviting space.

Cabin in Falmouth

4.67 out of 5 average rating, 617 reviews

Waterside Guest House

4.9 out of 5 average rating, 300 reviews

A view overlooking a well-maintained pool surrounded by green grass, with beach access visible in the distance. The landscape features a mix of trees and charming houses, set against a clear blue sky and tranquil water.

Home in Plymouth

Ocean Side, Amazing View, close to town/beach, Spa

Guest suite in Harwich Port

A cozy bedroom features a spacious bed adorned with a textured blanket. Air conditioning is visible on the wall, while a microwave is positioned beside a small refrigerator. Large glass doors lead to an outdoor deck with a seating area and vibrant flowers.

4.9 out of 5 average rating, 51 reviews

Harbor Getaway - #1

4.92 out of 5 average rating, 49 reviews

A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.

Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May 15

5 out of 5 average rating, 9 reviews

Home in Sandwich

Family Cape Oasis w/ Pool, Game Room & Kids' Room

Private, pet-friendly home rentals

5 out of 5 average rating, 72 reviews

A fire pit area features six sturdy blue Adirondack chairs arranged around a circular stone fire pit, overlooking a serene waterfront view. Lush greenery surrounds the area, with the calm water of Long Pond visible in the background.

Home in South Yarmouth

Sunburst Cottage on Long Pond

5 out of 5 average rating, 24 reviews

Home in Brewster

The Roost with path to beach

4.97 out of 5 average rating, 32 reviews

A wooden deck extends from the house, featuring a seated area with an Adirondack chair. Expansive views of the ocean and shoreline are visible, framed by low coastal vegetation and a wooden fence. A clear sky with scattered clouds creates a serene backdrop.

Home in Plymouth

Oceanfront Home on Cape Cod Bay with Beach Access

5 out of 5 average rating, 12 reviews

Spacious Chatham 4BR | Dog OK + Deck + Sleeps 10

A bright living area features a blue sectional sofa and a colorful coffee table with intricate designs. In the background, an open kitchen is visible with modern appliances and bar seating. Natural light enhances the spacious feel, complemented by light hardwood flooring.

5 out of 5 average rating, 84 reviews

Chatham: Tennis, water views/access, pet friendly!

A charming exterior view of a home features a well-maintained lawn with a swing hanging from a tree. The entrance showcases a front door with a lantern beside it, framed by lush green shrubs. A garage is visible to the right.

4.98 out of 5 average rating, 45 reviews

Chatham, MA - 6 Sabins Lane 5BR + Outdoor Shower

5 out of 5 average rating, 59 reviews

A rustic cottage is seen with a light-colored exterior and a shingled detailing. The porch features a small table surrounded by four chairs, while two lounge chairs sit nearby. Large windows allow natural light to enter, framed by a backdrop of trees.

Cottage in Wellfleet

Wellfleet Cottage By The Sea