Pet-friendly holiday rentals in Eastham

4.99 out of 5 average rating, 104 reviews

A charming cottage exterior is surrounded by lush green grass and vibrant flower boxes. The house features a shingle facade and windows adorned with traditional shutters. A tranquil garden area adds to the serene atmosphere, inviting guests to enjoy the peaceful surroundings.

Cottage in Orleans

Hobbit Cottage with Marsh View

Are you special enough to stay at the Hobbit Cottage? All of our tenants have been magical so far and we want to continue that trend! This cute little house is on a lovely marsh where you will hear birdsong while you enjoy the ever changing view of the gentle wetland. A mini paradise nestled in a quiet neighborhood, it is an easy bike ride or a short drive to Nauset Beach. Tiny and cozy, the cottage has every amenity for a comfortable stay! (7 Day SATURDAY - SATURDAY Minimum July 11 - Sep 5)

PetsWalkabilityLong stay

5.0 out of 5 average rating, 18 reviews

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

Outdoor spacesWalkabilitySleep quality

A charming exterior of a single-story home is framed by a well-maintained lawn and trees. A gravel pathway leads to a screened porch, where rocking chairs are visible. The attractive shingle siding is complemented by a brick chimney, and a small blue shed is present in the background.

4.92 out of 5 average rating, 13 reviews

Brook House on the Bay Side

Classic Cape Charm! Welcome to Herring Brook, a beautifully updated 2-bedroom, 1-bath cottage in the heart of Eastham. Sleeps 4. Enjoy new flooring, a spacious screened porch, wraparound deck, large yard, and classic Cape Cod outdoor shower. Features include an updated kitchen and bath, Wi-Fi, Smart TV, A/C, washer/dryer, linens, and beach chairs. Bay and ocean beaches, Cape Cod Rail Trail, restaurants, shops, and family attractions are just minutes away. Pets considered with prior approval.

Outdoor spacesPetsKitchen

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, 321 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.

Outdoor spacesWalkabilityComfort

4.96 out of 5 average rating, 69 reviews

A decorative sign features the text '1130 Time & Tides' in elegant script. The sign is set against a wooden shingle backdrop, highlighting its nautical theme with an image of a sailboat and waves, conveying a connection to the coastal location.

Cottage in North Eastham

Time and Tides on Cape Cod Bay

Relaxing TIME and spectacular TIDES is why so many come to outer Cape Cod Bay. That is exactly what you will find with our beautiful cottage. Just feet from the beach (40 second walk), you can stroll to the shore at any time. So many things to do and places to see just minutes away. Or do nothing but relax, take in the amazing sunsets and enjoy one of the most beautiful locations on Cape Cod. We welcome pets but there will be an additional $125.00 charge for cleaning. 2025 New AC added !!

Outdoor spacesPetsAccuracy

4.97 out of 5 average rating, 203 reviews

A charming cottage is surrounded by a grassy yard, featuring a set of four blue Adirondack chairs arranged around a small glass table. A gas grill is situated nearby, and a tree provides dappled shade to the area.

Guesthouse in Wellfleet

Abundant Blessings Cottage – Wellfleet

Couple/family fun all year in a charming, private Cape Cod cottage w/ screened in porch, patio & outdoor shower (in Nov/Dec/Jan becomes a Gingerbread cottage). Inside: open living space w/ queen bed & sitting space. Ladder leads to a short height sleeping loft w/ 2 twin beds. Full bathroom w/ indoor shower. Kitchenette- see description below. We supply tea, local coffee, spices, condiments, gas grill, ice chests, beach towels & chairs. To sleep up to 8, also rent our Upper Room on Airbnb.

PetsOutdoor spacesSolo travel

4.98 out of 5 average rating, 107 reviews

The exterior of the Brewster Farmhouse is showcased, featuring a charming stone facade with green trim. A well-maintained yard surrounds the house, adorned with autumn foliage. The entryway includes two large windows framed by shrubs, with a welcoming double door at the center.

Home in Brewster

Cape Cod Farmhouse: Walk to the Beach in Brewster!

Defined by understated furnishings throughout, The Brewster Farmhouse is a serene beach retreat, right across the street from Ocean Edge Resort and a 10 minute walk to Ellis Landing Beach. Total of 3 bedrooms and 4 full bathrooms, with central AC and heating. All bedrooms have queen-sized beds, and their own private, en-suite bathrooms. Right next door to cute antique shops, art galleries, and boutique farms. Close walk or drive to all of the best restaurants and cafes in Brewster!

Outdoor spacesPetsBiking

4.98 out of 5 average rating, 133 reviews

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

Outdoor spacesPetsLocation

4.93 out of 5 average rating, 164 reviews

Home in Brewster

4BR/3B | Walk2Pond | Screened Porch | FireTbl | AC

Relax at this spacious mid-Cape retreat on a quiet private road, just a 5-minute walk to a private swimming beach and pond. Canoe included! Sleeps 8 with 4 bedrooms (2 on the main level, 2 upstairs) and 3 full baths with bidets. Enjoy central A/C, hardwood floors, a screened porch, 65" OLED TV, gas stove, gas fire table and grill, ping pong, and wooded yard. Convenient main-level washer/dryer. Near the Cape Cod Rail Trail, beaches, golf, tennis, boating.

PetsOutdoor spacesHeating

A charming exterior of the Carriage House features weathered shingle siding and a cupola on the roof. Surrounded by landscaped gardens, the entrance showcases a well-kept pathway and a mix of greenery and blooming flowers, creating a welcoming ambiance.

4.96 out of 5 average rating, 207 reviews

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.

WalkabilityPetsLong stay

A charming cottage with a shingle exterior is set among tall trees. A covered porch with a railing invites relaxation. Large front windows provide ample natural light, while stone steps lead to the entrance. Surrounding landscaping features a mixture of gravel and greenery.

4.92 out of 5 average rating, 38 reviews

Dog friendly, close to bay beaches & bike path

Welcome to Bralla by the Bay, an Outer Cape 4 bedroom cottage that is only half a mile to the beautiful bay beaches and a 5 minute drive to both the National Seashore and kettle ponds. Our cottage is located in a quiet, wooded quintessential Cape Cod neighborhood which offers easy access to beach, nature, and dining activities. It is cozy, yet spacious enough to accommodate a larger group with its ample parking and yard.

WalkabilityOutdoor spacesHiking

A charming, light-colored house sits under a clear sky, surrounded by trees. The front entry features a welcoming pathway, two white Adirondack chairs, and a small table with flower pots. Large windows provide views into the interior, while a well-maintained garden enhances the curb appeal.

4.86 out of 5 average rating, 133 reviews

Walk to Beach, Pet Friendly, New Fenced Backyard!

Welcome to The Library! This newly renovated Eastham home is just a short walk to Thumpertown Beach and a quick drive to the National Seashore. Enjoy a redesigned eat-in kitchen, a screened-in three-season room, and a fully fenced backyard with brand-new pavers, a fire pit, and space for kids and dogs to play. Pet friendly and perfect for relaxing—come unwind and enjoy the best of the Cape

PetsOutdoor spacesHiking

Popular amenities for Eastham pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.99 out of 5 average rating, 337 reviews

A private waterfront deck offers a serene view of Flax Pond, surrounded by lush greenery. Adirondack chairs are positioned for relaxation, providing a perfect spot to enjoy the tranquil waters and natural surroundings.

Home in Dennis

Stunning Waterfront with Serene Sunrise Views!

PetsOutdoor spacesKitchen

4.99 out of 5 average rating, 68 reviews

Seaside Seaduction~On the water/Dog Friendly

WalkabilityOutdoor spacesIndoor spaces

5.0 out of 5 average rating, 15 reviews

Stay On The Cape Vacation Rentals, Cape Cod Getawa

WalkabilityPetsNearby

5.0 out of 5 average rating, 8 reviews

Home in Wellfleet

Wellfeet Retreat

WalkabilityPetsKitchen

5.0 out of 5 average rating, 26 reviews

Meadow + Main

PetsBeachSleep quality

A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.

5.0 out of 5 average rating, 29 reviews

The Chatham Bars White Foam House Steps From Beach

Outdoor spacesWalkabilityComfort

4.98 out of 5 average rating, 65 reviews

No Pet Fee, Waterfront, Fenced Yard, Close to Town

Outdoor spacesPetsBarbecue

5.0 out of 5 average rating, 22 reviews

A serene landscape is displayed with lush green marshlands reflecting the soft colors of the sunset. Gentle waterway patterns create a tranquil ambiance, while trees line the background, enhancing the natural beauty of the scene.

Home in Wellfleet

Marsh Side Home with Stunning Sunset View

Outdoor spacesViewSleep quality

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 51 reviews

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

WalkabilityOutdoor spacesAir conditioning

5.0 out of 5 average rating, 42 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

Harwich Haven: Pool & Fire Pit

WalkabilityPetsPool

4.92 out of 5 average rating, 52 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-Oct

Outdoor spacesWalkabilityCheck-in

5.0 out of 5 average rating, 10 reviews

Home in East Dennis

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Outdoor spacesCleanlinessKitchen

4.89 out of 5 average rating, 18 reviews

Apartment in Dennis Port

Dennis Deluxe King Room | Full Studio w/ Kitchenet

Outdoor spacesPetsHospitality

4.97 out of 5 average rating, 31 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

PetsWalkabilityHospitality

4.97 out of 5 average rating, 31 reviews

A refreshing swimming pool is surrounded by a concrete deck, featuring several lounge chairs positioned along one side. Umbrellas provide shade near the pool's edge, and a fenced yard is adorned with greenery, creating a serene outdoor setting.

Home in Barnstable

Beach Pass Included! Brand New Spa! Central AC!

WalkabilityOutdoor spacesCondition

4.94 out of 5 average rating, 53 reviews

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

Coastal Charm New Seabury: 5BRs with Private Pool

Outdoor spacesWalkabilityLocation

Private, pet-friendly home rentals

4.82 out of 5 average rating, 38 reviews

A spacious cedar deck is furnished with a picnic table and two wooden lounge chairs, surrounded by greenery. The cottage features a screened-in porch with large windows, allowing natural light to illuminate the interior while blending outdoor and indoor living.

Cottage in Eastham

1940 Cottage Studio/Loft Style Stunner! Dogs ok!

WalkabilityPetsComfort

4.98 out of 5 average rating, 48 reviews

A cozy living area features a gray sofa, two white armchairs, and a round coffee table. A wall-mounted television is visible, along with decorative fish artwork. Natural light enters through large windows, enhancing the neutral color palette and inviting atmosphere.

Cottage in North Eastham

The BayBreeze

PetsOutdoor spacesNearby

5.0 out of 5 average rating, 82 reviews

The modern guest suite features a spacious deck with outdoor seating, surrounded by natural landscaping. Large windows allow ample natural light, and the structure blends harmoniously with the surrounding pine and oak trees under a clear blue sky.

Guest suite in Truro

New 2 Bedroom Modernist Oasis in Truro

WalkabilityPetsTV

4.77 out of 5 average rating, 13 reviews

The open living area includes two couches positioned facing each other, with a small side table nearby. Light wood flooring extends to a dining area featuring a white table and chairs. Soft natural light is visible through the windows, highlighting the light-colored walls.

Holiday home in Brewster

Bright 3 bdrm 2 bath on Bike Trail, 5 min to Beach

WalkabilityOutdoor spacesBathroom

4.99 out of 5 average rating, 73 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

WalkabilityPetsBathroom

The exterior of a charming house is framed by lush gardens featuring colorful flowers and greenery. A red umbrella provides shade over an outdoor seating area, while a playful swing is visible in the background. The structure showcases a blend of natural wood siding and a shingled roof.

4.91 out of 5 average rating, 45 reviews

Serene Escape on Cape Cod -Bayside - Dog Friendly

WalkabilityOutdoor spacesAccess

A classic cape-style home is nestled within a wooded landscape, showcasing a shingled exterior and a dark blue front door. A small deck extends from the side, accompanied by outdoor seating. Natural surroundings create a peaceful atmosphere with minimal grass and scattered trees.

4.9 out of 5 average rating, 48 reviews

Cape Cod home near National Seashore and bike path

PetsOutdoor spacesKitchen

A sandy beach is lined with beachgoers enjoying the sun, and colorful umbrellas provide shade. Gentle waves ripple in the water under a clear blue sky, while grassy dunes frame the scene, highlighting the natural beauty of the coastal location.