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

LUX Designer Private Waterfront
Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

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!

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

Rustic Pebble Cottage in beautiful Bridgton, Maine
Pebble Cottage is a one hundred year old quirky camp that was enlarged some years back. It is located in Bridgton near plenty of lakes and skiing. The public beach is a short skip down the hill. The cottage is a rustic little haven that was saved from demolition, and updated with a brand new bathroom, a cute little kitchen with a dishwasher, with two heat pumps to keep the space cozy and three homey comfortable bedrooms, a large yard with a hammock, very quiet retreat. Please note it's old!

Lake House with a View!
Lovely 3 bedroom/2.5 bathroom lakefront house! Watchic Lake is a perfect family destination for swimming, boating, and fishing. Perfectly located for a day trip to Portland, Old Orchard Beach, Kennebunkport, Freeport, Kittery, Wells Beach, and North Conway, NH outlets. Beautiful views of the lake from each room, w/full kitchen, laundry, 3 TVs. As our guest, you will have access to a private boat launch. In the winter snowmobile, snowshoe, ice skates, or cross-country ski on the frozen lake.

Waterfront Private Apartment just 5 min to LLBean!
Guest apartment with king bed, private entrances, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Take it easy in the woods at this cozy, off-grid A frame located in the Sebago Lakes Region. Kick back and relax around the fire while being "away from it all" yet still close by to great restaurants, beaches and more! This cabin is "off grid" and does not have running water or electricity. The space offers solar power that will power all lights, fans as well as charge devices. There is a battery operated pump that gives you potable water out of the sink. A porta potty is on property.

Steep Falls Escape, river & falls just steps away
Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

Sunset Haven - Little Sebago Lake
Sunset Haven is a beautiful 3BR, 1.5 bath year round lakeside cottage on Little Sebago Lake in Gray, Maine. It boasts a private beach and water frontage in the heart of Maine's Sebago Lakes Region. Located only about half an hour max from Portland, Maine and the Atlantic coastline, approximately an hour or less from Shawnee Peak and the Sunday River Ski areas, 40 minutes from Oxford Casino, this area is truly a great destination for four season recreation.

Secluded, cozy cabin nestled in the Maine woods
Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.

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.

Cozy 2 BR Apt in Walking Distance to Restaurants
This is a private two bedroom apartment in a great location (15 minutes to downtown Portland). The apartment is in walking distance to eateries, Riverbank Park, grocery stores and local breweries. It is also located across the street from the police station on a dead end street. The unit is child friendly and has a pack 'n Play and high chair. (Please note that linens are not provided for the Pack n’ Play.)
Popular amenities for Windham pet-friendly home rentals
Pet-friendly house rentals

Newly renovated 3BR house w/ stunning ocean views

Fish Tales Cabin

Mountain View Home | Steps to Hiking & Waterfalls!

Hallowell Hilltop Home and Hot Tub

Winter Dates: Cozy and Peaceful Island Getaway

Entire House in Portland!

The Watson House

#1 View in Maine, Theater, HTub, Xbox, Putting Grn
Pet-friendly home rentals with a pool

White Mountains Hiking Dogs Storyland Family

Ski, snowboard, skate, hike, clubhouse and more

Charming Chalet 3 min to SKIING & PVT beach access

Spacious Condo-Attitash Ski-Storyland-Saco & More!

Cozy Top Floor-1 King, Mtn View, Jetted Tub, Pools

The 1785 Suite, Amazing Views, Walk to River

Two Bedroom Two Bath Cabin

Centrally located, Spacious: Ski, Hike, Swim, Bike
Private, pet-friendly home rentals

Beachfront on Highland Lake- close to Portland

Beautifully, Gambrel style home

The Purple House by Pettingill Pond

Woodland with Fireplace Home

Lakehouse on Highland Lake

Crescent Beach Gardens

Large, luxurious geodesic dome - 04

Mountain View Studio
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $422 CAD | $377 CAD | $322 CAD | $330 CAD | $333 CAD | $434 CAD | $478 CAD | $519 CAD | $422 CAD | $351 CAD | $422 CAD | $392 CAD | 
| Avg. temp | -6 °C | -4 °C | 1 °C | 6 °C | 12 °C | 18 °C | 21 °C | 20 °C | 16 °C | 10 °C | 4 °C | -2 °C | 
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 $112 CAD per night before taxes and fees

Verified guest reviews
Over 2,150 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Windham vacation rentals include wifi 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!
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- Rentals with lake access Windham
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 - Pet-friendly rentals Cumberland County
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 - Pet-friendly rentals United States
 
- Ogunquit Beach
 - Sebago Lake
 - Wells Beach
 - Story Land
 - Scarborough Beach
 - York Harbor Beach
 - Attitash Mountain Resort
 - Long Sands Beach
 - Popham Beach State Park
 - Popham Beach, Phippsburg
 - Pemaquid Beach
 - Diana's Baths
 - East End Beach
 - Pemaquid Point Lighthouse
 - Dunegrass Golf Club
 - Funtown Splashtown USA
 - Willard Beach
 - Coastal Maine Botanical Gardens
 - Parsons Beach
 - Wolfe's Neck Woods State Park
 - King Pine Ski Area
 - Short Sands Beach
 - White Lake State Park
 - Ferry Beach