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Pet-friendly vacation rentals in Windham

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in Windham

  • Total vacation rentals

    Explore 60 vacation rentals in Windham

  • Nightly prices starting at

    Windham vacation rentals start at R 1,294 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 2,570 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Windham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windham rentals

  • 4.8 Average rating

    Windham stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated pet-friendly home rentals in Windham

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.
Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

WalkabilityOutdoor spacesParking

4.92 out of 5 average rating, 132 reviews
Top guest favorite
Home in Bridgton

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Perched at the summit with complete privacy and sweeping views of Mount Washington, the White Mountains, and Woods Pond, Mainely Mountain Views is a 4-bedroom Maine retreat that earns its name the moment you step onto the deck. Perfect for large groups with easy access to Pleasant Mountain, Long Lake, Sebago Lake, and the Saco River - plus hiking, mountain biking, and snowmobile trails. Watch the sun set over the mountains from the hot tub. The kind of place you come to relax, unwind, and enjoy.

Outdoor spacesPetsCheckout

4.95 out of 5 average rating, 271 reviews
Guest favorite
A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.
Home in Falmouth

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

WalkabilityPetsComfort

4.9 out of 5 average rating, 331 reviews
Top guest favorite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

PetsWalkabilityParking

4.96 out of 5 average rating, 179 reviews
Superhost
A spacious dining area is highlighted by a wooden table surrounded by white chairs. A staircase with wooden railings leads to the upper level. Natural light fills the room through multiple windows, enhancing the warm wooden details of the walls and floor.
Loft in Portland

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

PetsWalkabilityParking

4.89 out of 5 average rating, 377 reviews
Top guest favorite
A bright living space features a comfortable dark sofa facing a small wooden coffee table. A round dining table with two chairs is visible in the background. Large windows allow natural light to fill the room, complemented by pale curtains and wooden flooring.
Cottage in Windham

The Purple House by Pettingill Pond

Welcome to Maine. The way life should be! The Purple House (bc the paint color is a happy shade of light purple) is 2 floor home ACROSS the gravel road from Pettingill Pond. Less than 100 ft away from the dock with SHARED access with two super friendly neighbors in the Summer. As a guest of this house you have access to this pond where it is perfect for swimming, rowing, kayaking, canoeing, paddle boarding, boating, floating, ice skating, & snow shoeing. Quick 5 mins from the city center!

PetsWalkabilityHeating

4.9 out of 5 average rating, 102 reviews
Top guest favorite
A serene waterfront scene is presented, showcasing a calm lake framed by trees. In the foreground, a small dock extends into the water alongside a moored boat. Rocky shorelines feature boulders partially submerged, adding to the natural beauty of the landscape.
Guest suite in Raymond

Sebago Lake Waterfront Studio

Beautiful Lakehouse studio apartment located on Sebago Lake. A perfect spot to take in the gorgeous lake view w/sandy beach. The lake is great for swimming, boating, kayaking, and water activities. Backyard to enjoy lawn games, grill, and relax by the outdoor fire-pit. This space has a cozy modern feel, for a perfect summer vacation or fall leaf-peeping. Located within 40 minutes of Portland and the beautiful Maine coast. This space is furnished to sleep 4. Dock available for $100 per stay.

Outdoor spacesWalkabilityCleanliness

4.96 out of 5 average rating, 105 reviews
Guest favorite
Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

PetsOutdoor spacesGetting around

4.98 out of 5 average rating, 200 reviews
Top guest favorite
A wooden dock extends toward calm water, with a gentle sloping pathway leading down from the boathouse. The clear water reveals stones at the bottom, while green trees frame the picturesque lakeside view.
Guesthouse in New Gloucester

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

Outdoor spacesPetsQuiet

4.9 out of 5 average rating, 178 reviews
Guest favorite
A spacious dining area features a wooden table surrounded by six chairs, illuminated by natural light through large windows. Soft curtains frame the windows, and a decorative fishing net hangs on the wall. The kitchen is partially visible, showcasing modern cabinetry.
Home in Standish

New and Spacious Family Home Close to Sebago Lake

Full of light and thoughtful touches, this giant five bedroom home is perfect for your Sebago Lake getaway. Spend your evenings relaxing or entertaining on the spacious deck and days on the water. Perfect for family fun and couples' retreats, this home is a fantastic home base to explore the Sebago Lake Region. Enjoy a fully air conditioned home with mini splits in every room. Bedrooms include 4 King, 1 Full, and 5 Twin beds. Bathrooms include 2 walk in showers and one bathtub.

PetsWalkabilityCleanliness

4.88 out of 5 average rating, 109 reviews
Superhost
A spacious living area features a sectional sofa in soft brown upholstery, accented with decorative pillows. A black coffee table displays a decorative centerpiece, while a floor lamp adds light. The room is complemented by light grey walls and modern decor.
Guesthouse in Westbrook

Modern stay Westbrook Maine

Welcome to our modern 1-bedroom basement retreat, nestled in the charming town of Westbrook, just a short 3-minute drive from the Portland, Maine. With its stylish design and upscale amenities, this Airbnb offers the perfect blend of comfort and convenience for your stay in the area. The bedroom features a Queen-size bed, a queen-size pull-out sofa in the living area, accommodating additional guests comfortably in the spacious living area. There’s a $200 pet fee per pet.

PetsWalkabilityComfort

4.82 out of 5 average rating, 138 reviews
Top guest favorite
A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.
Chalet in Standish

Blueberry Hill

Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.

PetsOutdoor spacesCondition

4.96 out of 5 average rating, 263 reviews

Popular amenities for Windham pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favorite
An airy living space is highlighted by tall windows that bring in natural light and showcase views of the surrounding trees. A large sectional sofa faces a flat-screen TV, complemented by a wood stove for warmth. A dining area is visible in the background.
Home in Freeport

Waterfront 5 BR Home | On Casco Bay in Freeport!

Outdoor spacesPetsWifi

4.96 out of 5 average rating, 147 reviews
Top guest favorite
The exterior of a modern oceanfront home is captured, showcasing a two-story structure with light gray siding and a charming front entrance. Lush landscaping and a paved driveway enhance the appeal. Panoramic views of the beach and ocean are visible in the background.
Home in Old Orchard Beach

Unique and Stunning Beachfront property Greygoose

Outdoor spacesPetsParking

4.92 out of 5 average rating, 189 reviews
Top guest favorite
An open living area is highlighted by large windows that frame scenic views of the marsh. A modern gas fireplace serves as a focal point, while a light-colored sofa and a small table with a plant create a welcoming ambiance. Bar seating for four extends to the kitchen.
Home in Higgins Beach

Higgins Beach *New* Beach Home & Private Offices

PetsWalkabilityBeach

5.0 out of 5 average rating, 115 reviews
Guest favorite
A bright living area features a wooden floor and a cozy, gray sofa. A blue writing desk is positioned beside a window, adorned with decorative bookshelves and plants. A vintage-style wood stove is set against a brick wall, with warm light enhancing the inviting atmosphere.
Home in Freeport

Charming Historic Freeport House

Outdoor spacesWalkabilityAccuracy

4.89 out of 5 average rating, 114 reviews
Guest favorite
The living area features high, wooden ceilings with exposed beams and large windows, allowing natural light to flood the space. A stone fireplace serves as a focal point, while a cozy seating area is complemented by a dining table surrounded by red chairs.
Home in Naples

Best Ski & Lake House

Outdoor spacesPetsAccess

4.94 out of 5 average rating, 140 reviews
Guest favorite
A serene vista showcases the city skyline reflected in calm waters, framed by lush green grass and trees. The scene captures a tranquil moment, inviting viewers to appreciate the natural beauty and urban blend surrounding the space.
Home in Portland

Top Deck - Portland Property with Views!

PetsWalkabilitySkiing

4.92 out of 5 average rating, 305 reviews
Top guest favorite
An open-concept living area features exposed wooden beams and large windows that provide natural light. A comfortable sofa and armchair are arranged around a coffee table, with a dining area visible in the background. The kitchen showcases modern appliances and a spacious layout.
Home in Portland

Entire House in Portland!

WalkabilityOutdoor spacesCondition

4.97 out of 5 average rating, 298 reviews
Top guest favorite
Home in Limerick

Lakefront Getaway

Outdoor spacesWalkabilityView

4.93 out of 5 average rating, 150 reviews

Pet-friendly home rentals with a pool

Guest favorite
A welcoming living area features warm wood flooring and natural light from multiple windows. Comfortable seating includes a sofa and chairs arranged around a central table. A ceiling fan provides gentle airflow, while double French doors lead to an outdoor space.
Guest suite in Standish

Steep Falls Escape, river & falls just steps away

Outdoor spacesPetsComfort

4.92 out of 5 average rating, 125 reviews
Guest favorite
The modern cabin features a sleek design surrounded by lush greenery. Soft bistro lights create a warm glow, illuminating the outdoor seating area with two Adirondack chairs. The deck can be seen in the background, enhancing the inviting atmosphere of the natural setting.
Cabin in Freeport

Romantic hideaway cabin w/ access to spa - 26

Outdoor spacesWalkabilityParks

4.96 out of 5 average rating, 125 reviews
Top guest favorite
Place to stay in Shapleigh

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

PetsWalkabilityAccess

5.0 out of 5 average rating, 145 reviews
Guest favorite
A luxurious queen bed is adorned with intricate linens and decorative pillows. Two bedside lamps provide soft lighting, and large windows dress the space with natural light, framed by sheer curtains that enhance the overall elegance.
Apartment in Cape Elizabeth

Portland & Beach & Lighthouses! Romantic! Lovely

WalkabilityPetsBathroom

4.87 out of 5 average rating, 615 reviews
Guest favorite
A cozy room features beige walls with subtle lines, accented by a large round mirror. A small kitchenette is equipped with a microwave and refrigerator. A spacious bed with red accents is arranged near bright windows, while a wooden dresser and a light-colored chair complete the space.
Apartment in Conway

NoCo Village King/Jacuzzi

PetsOutdoor spacesValue

4.89 out of 5 average rating, 401 reviews
Guest favorite
A spacious living area features warm wood paneling and a cozy wooden fireplace. Comfortable seating is arranged around a coffee table, and large glass doors allow natural light to fill the room, leading to the scenic outdoors. A ladder provides access to the loft area.
Chalet in Bridgton

Charming Chalet 3 min to SKIING & PVT beach access

Outdoor spacesWalkabilityLong stay

4.87 out of 5 average rating, 130 reviews
Guest favorite
The exterior of a restored cottage is showcased with light shingle siding and a covered front porch. Vibrant flowerbeds are highlighted along the walkway, and a wooden arch frames the entrance. Lush green grass surrounds the home, complemented by a white picket fence.
Home in Gorham

Top Notch Inn | Mt. Moriah Cottage

Outdoor spacesWalkabilityGetting around

4.88 out of 5 average rating, 103 reviews
Guest favorite
A spacious loft area with a vaulted ceiling features large triangular windows that provide expansive views of the surrounding landscape. Natural wood accents enhance the warmth of the space, creating a bright and airy atmosphere complemented by an inviting seating arrangement below.
Cabin in Bethel

POOL+Hot tub+6Private Acres+15 min to Sunday River

PetsOutdoor spacesValue

4.95 out of 5 average rating, 97 reviews

Private, pet-friendly home rentals

Top guest favorite
A serene waterfront scene captures calm waters dotted with boats gently bobbing in the harbor. Rocky shores lead to lush greenery in the background, with a clear blue sky above, creating an inviting coastal atmosphere in this Maine setting.
Apartment in Falmouth

Falmouth Waterfront Carriage House Apt

PetsWalkabilityParking

4.97 out of 5 average rating, 200 reviews
Top guest favorite
The exterior of the guest suite is shown, featuring a stone pathway leading to a glass door. Landscaping includes a decorative planter and natural stone elements, surrounded by greenery. A wooden fence provides privacy, creating a welcoming entryway to the space.
Guest suite in North Yarmouth

open concept Guest Suite in southern Maine

PetsWalkabilityAmenities

4.97 out of 5 average rating, 151 reviews
Superhost
Cottage in Harpswell

Quaint & Peaceful Designer's Oceanfront Cottage

PetsWalkabilityParking

4.86 out of 5 average rating, 242 reviews
Top guest favorite
Adirondack chairs are arranged in a semi-circle on lush green grass, facing a calm lake. The clear blue sky reflects in the water, with autumn leaves scattered on the ground, creating a serene lakeside atmosphere.
Home in Windham

Rise & Shine - Breathtaking Sebago Lake view

Outdoor spacesComfortLocation

4.95 out of 5 average rating, 63 reviews
Top guest favorite
A calm Highland Lake is depicted with a reflective surface, capturing the surrounding trees and clouds. Bright autumn foliage colors the landscape, blending with the serene waters. Gentle ripples can be observed, enhancing the peaceful ambiance of this natural setting.
Home in Windham

Lakehouse on Highland Lake

Outdoor spacesWalkabilitySkiing

4.97 out of 5 average rating, 90 reviews
Top guest favorite
A charming house exterior is shown, featuring a gable roof and a red door. Windows adorn the upper level, and an air conditioning unit is visible. A wooden porch leads to the entrance, complemented by a charcoal grill and an American flag displayed on the porch.
Home in Windham

Cozy Camp on the lake

Outdoor spacesPetsHiking

4.98 out of 5 average rating, 62 reviews
Top guest favorite
Cottage in Windham

Cozy Maine Lakefront Paradise

PetsOutdoor spacesBackyard

4.96 out of 5 average rating, 25 reviews
Guest favorite
Apartment in Windham

Lakeside Suite | Private | Projector Theater

PetsTVKitchen

5.0 out of 5 average rating, 19 reviews

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 4,045 ZARR 4,028 ZARR 4,530 ZARR 4,951 ZARR 4,045 ZARR 4,853 ZARR 5,501 ZARR 5,970 ZARR 4,853 ZARR 4,190 ZARR 4,643 ZARR 4,611 ZAR
Avg. temp-6°C-4°C1°C6°C12°C18°C21°C20°C16°C10°C4°C-2°C

Destinations to explore