Pet-friendly holiday rentals in Eastham

4.83 out of 5 average rating, 30 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!

Charming stand alone Cape Cod Cottage, part of the historic Cottage Grove cottages of Eastham. A perfect respite for the busy world! The open and airy cottage exudes character: exposed beams, vaulted ceilings, fireplace, and a vintage soapstone sink. The wall of windows leads out to the spacious private cedar deck with picnic table and chairs for outdoor dining or relaxing among the trees. Cottage is dog friendly and located near the celebrated Fort Hill hiking trails at the National Seashore.

4.98 out of 5 average rating, 363 reviews

Tiny home in Wellfleet

Writer’s Cabin • On-Site Spa w/ Hot Tub & Massage

Our beloved “piece of heaven on earth” is a cabin-style tiny home filled with books—perfect for writers or a relaxing beach getaway. Perched on a gentle incline, the Writer’s Retreat feels private and tucked away among the trees. Just minutes’ drive from beaches and a short stroll to the charming center of Wellfleet. Unwind at our on-site SeaRose Spa, w/ a hot tub, saunas, & massage therapy (special guest rates) — part of our BnB property, which also includes two guest suites in the main house.

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.

4.9 out of 5 average rating, 10 reviews

Brook House on the Bay Side

Welcome to this recently updated, charming 2-bedroom, 1-bath home in Eastham — the perfect Cape Cod getaway. Recent improvements include fresh paint, new bathroom and kitchen. TV and Wi-Fi. Start your mornings with coffee on the large sunny screened porch, enjoy your own private outdoor shower. Washer/ dryer are available on site. Bay-side beaches, freshwater ponds, local park, mini golf, arcade, pizza, ice cream, local shops, ocean beaches, rail trail, historic sites, 1 to 3 mile radius.

5 out of 5 average rating, 5 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!

4.98 out of 5 average rating, 103 reviews

The exterior of the beach house displays a welcoming porch adorned with two light blue Adirondack chairs and a small table. A bird feeder hangs nearby, while a decorative lantern and a birdbath provide additional charm. The entryway features a bright yellow door with a sign reading 'Cottage.'

Cottage in North Eastham

Cottage Getaway walk to beach

This Cute As Can Be Beach House is looking for guests! Just a five minute stroll to the beach, The Cottage is the perfect spot for a getaway. Open floor plan with spacious living-room, two bedrooms and bath. Large yard with outdoor shower and a hammock big enough for two! Includes beach chairs, towels, cooler. A true gem! Amenities -Air Conditioning -Heat -Smart TV -Wi-Fi -Gas grill/firepit -Two patios -Washer/Dryer -Outdoor shower - Parking -Adirondack chairs -Amazing sunsets

4.98 out of 5 average rating, 101 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!

A charming 1940s Cape Cod cottage is surrounded by greenery and trees, with a white exterior featuring traditional shingles. The front garden includes flowers and a seating area. A wooden fence runs along the property, adding to the serene, natural atmosphere.

4.95 out of 5 average rating, 22 reviews

Sweetbriar ~ Charming Cape Cottage ~ Dog-Friendly!

Discover Sweetbriar, a 1940s two-bedroom 600 sqft Cape Cod retreat in Eastham’s peaceful Cottage Grove. Minutes from First Encounter Beach and Fort Hill, this cozy, dog-friendly cottage blends classic charm with modern comfort. Relax on the private deck, explore scenic bike trails, and unwind in a warm, inviting space. With easy access to beaches, villages, and nature, Sweetbriar offers the perfect escape for unforgettable Cape Cod days. Book now and experience the magic of the Cape!

5 out of 5 average rating, 125 reviews

Home in Yarmouth Port

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

4.89 out of 5 average rating, 349 reviews

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.

Apartment in Brewster

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!

Superhost

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, 196 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.

4.9 out of 5 average rating, 51 reviews

Guest house in Brewster

Cape Cod beach inspired “Makondo” Suit Apartment!

Private, beach-inspired suite perfect for couples or small families. Makondo is fully independent with its own entrance, outdoor space, and parking. Relax in a bright coastal interior with full kitchen, washer/dryer, AC, and comfy sleeping options. Minutes to Cape Cod beaches, walking trails, and local attractions. Peaceful, clean, and thoughtfully designed for a relaxing getaway. Pet friendly (fee applies).

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, 127 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

Popular amenities for Eastham pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 23 reviews

An outdoor fire pit, surrounded by four white Adirondack chairs, sits on a stone patio. Stone landscaping features greenery and flowering plants in the background, providing a serene setting for gatherings. The flames add warmth to the inviting atmosphere.

Home in Chatham

Beautifully renovated home, outdoor space, pets ok

4.9 out of 5 average rating, 84 reviews

A modern kitchen features butcher block counters and a spacious island. Black cabinets and white cabinetry provide a clean contrast. A dual range with a double oven is present. Multiple windows allow natural light, and artwork adorns the walls. Dining areas with tables and black chairs are visible.

Home in Brewster

Brewster Hideaway

4.94 out of 5 average rating, 50 reviews

A dining area features a light-colored table adorned with a floral centerpiece and a decorative sailboat. White chairs surround the table, which is set against a backdrop of a softly-lit, inviting space. A glimpse of a living room is visible through the framed opening.

Home in Harwich

Relaxing Harwich retreat with beautiful back yard

4.98 out of 5 average rating, 48 reviews

The exterior showcases a charming house with shingle siding and expansive windows. A wooden deck extends from the upper level, while a light-colored patio table with an umbrella is positioned on a lower terrace. Lush green grass surrounds the property, accented by shrubbery.

Home in Truro

1850's North Truro Farmhouse, Cape Cod

4.92 out of 5 average rating, 98 reviews

Home in East Dennis

** East Dennis - Perfect Spot - Historic Rte 6A **

5 out of 5 average rating, 7 reviews

A spacious, grassy backyard is surrounded by mature trees and specimen plantings. A charming shed and a statue are visible in the foreground, while the two-story house is seen in the background, partially shaded by the trees.

Home in Wellfleet

Home in Wellfleet

5 out of 5 average rating, 16 reviews

Home in Chatham

Meadow + Main

Superhost

Home in Harwich

5 out of 5 average rating, 4 reviews

Cape Cod Historical Oasis | Mecarta Farm

Pet-friendly home rentals with a pool

5 out of 5 average rating, 35 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

4.91 out of 5 average rating, 35 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.

4.88 out of 5 average rating, 92 reviews

A lagoon-style pool surrounded by a concrete deck provides lounge chairs and shaded areas under umbrellas. A gazebo is visible in the background, complementing the lush greenery that borders the property.

Villa in Wareham

Perfect Farmhouse for groups-golf/trails/beach

4.96 out of 5 average rating, 23 reviews

Home in Sandwich

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

5 out of 5 average rating, 10 reviews

Game Room- Movie Projector Room- Fire Pit

4.84 out of 5 average rating, 389 reviews

A hot tub emits a soothing green glow, surrounded by softly illuminated string lights. The tranquil outdoor setting features trees in the background and hints of nearby greenery, creating a relaxing atmosphere for evening enjoyment.

Home in Plymouth

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

4.91 out of 5 average rating, 161 reviews

A heated indoor pool is framed by sleek gray walls and illuminated with recessed lighting. Large sliding glass doors offer a view of the outdoor patio. Colorful pool floats and equipment are neatly arranged nearby, providing options for leisure activities.

Home in Plymouth

Seaview Summit | Ocean Views, Indoor Pool, Beach

Guest suite in Harwich Port

A modern kitchen is highlighted by light cabinetry and a granite countertop. A wall-mounted television is positioned for viewing, while natural light streams through a nearby window. Decorative nautical elements, including a ship model and coastal-themed items, are placed on the counter and in a woven basket.

4.97 out of 5 average rating, 60 reviews

Endless Summer - #3

Private, pet-friendly home rentals

Cottage in North Eastham

4.9 out of 5 average rating, 10 reviews

Salt N’ Pepper Cottage walk to Cape Cod Bay Beachs

4.96 out of 5 average rating, 28 reviews

Cape Charmer 4-2 sleep 10, 2 miles beach, Sun-Sun

A stack of vintage books is displayed, featuring titles related to marine life and fishing. The top book is accompanied by a decorative turtle. A golden decorative item resembling a fish is positioned nearby, adding an interesting textural element to the arrangement.

4.89 out of 5 average rating, 64 reviews

Quiet Cape Cod retreat on bike trail

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.

4.98 out of 5 average rating, 163 reviews

Spring Discount-Bay Beach, Sunsets, Dog Friendly.

A charming cottage is seen from the front, featuring a shingle exterior and blue shutters. The landscaped yard includes neatly trimmed shrubs and a decorative flower. A gravel driveway leads to the entrance, which is framed by two large windows and a welcoming front door.

4.91 out of 5 average rating, 23 reviews

Peaceful Beach Cottage with Deck & Firepit

4.97 out of 5 average rating, 66 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

5 out of 5 average rating, 75 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