
Family-friendly holiday rentals in Windham
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Windham

Total holiday rentals
Explore 130 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at $130 AUD per night before taxes and fees

Verified guest reviews
Over 5,500 verified reviews to help you choose

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
130 of Windham holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windham rentals

4.9 Average rating
Windham stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Windham
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Waterfront Gem walkable to Restaurants!
Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.
FamilyKitchenNearby

Dreamy Post&Beam Hideaway Near Portland & Freeport
Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.
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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.
Indoor spacesFamilyHeating

Edgewater Retreat - Lakefront w/Sauna & EV Charger
Welcome to Edgewater Retreat! This custom-built cottage features lakefront views and access to three beaches: secluded pocket beach in front of cottage, boaters beach with docks, and a full sun sandy bottom swim beach. Enjoy an unforgettable Maine vacation. Paddlecraft on the water, lounge in the hammocks, S'mores by the campfire, canoe to nearby island for offshore yoga, and gril with friends & family. In winter, enjoy ice fishing and kids enjoy snow sledding on adjacent hill.
Indoor spacesFamilyAir conditioning

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!
KitchenIndoor spacesBathroom

The Barnhouse with hot tub
Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.
FamilyKitchenHot tub

Sebago Sunrise Yurt - Trail Access!
Nestled between Portland's fine dining and Sebago's outdoor fun, the Sunrise Yurt is a great camping spot to explore what Southern Maine has to offer. Park & take a short walk to the back 2 acres of my property. The yurt overlooks a meadow & faces the sunrise. Located with access to the Sebago to the Sea Trail - 28 miles of walking & biking paths. .5 mile walking distance to Presumpscot River. *Please read 'Show More' notes section for important details.
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Cozy camp near highland lake
If you're looking for a quiet, cozy get a-way steps from the lake this is the place. Lake is private with no public access so it’s not crowded. Close to everything but far enough away; highway (95), Portland, Sebago Lake Area. Boating, swimming, fishing, hiking at your finger tips. 4 kayaks provided. Big yard, great for games, BBQ or sitting by the fire pit. Listen to the loons from the front deck. Sorry no pets so please don’t ask if you bring one!
FamilyKitchenPets

Sebago Lakehouse: Hot Tub and Private Beach Access
Lovely 3 bedroom/2 bathroom house in the woods with a Hot Tub and access to the private shared beach! Sebago Lake is a perfect family destination for swimming, boating, and fishing. It is ideally located for a day trip to Portland, Old Orchard Beach, Kennebunkport, or Freeport. Or stay home, enjoy the Lake or watch the stars from the Hot Tub. Close to grocery stores and restaurants. Lake and beach access is only a 5-minute walk.
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The Garden Cabin Tiny Home
Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018
FamilyKitchenValue

Cottage Under a Crabapple Tree
Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.
Indoor spacesKitchenBackyard

Cozy Rock Cabin #thewaylifeshouldbe
*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!
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Popular amenities for Windham family-friendly rentals
Family-friendly home rentals with a hot tub

LuxuryTreehouse w/ Hot Tub Near Sunday River
FamilyKitchenSleep quality

Cozy, romantic cabin overlooking a stream - 25
Indoor spacesFamilyOutdoor spaces

Luxe Lodge in the Woods! With Sauna & Hot tub
Indoor spacesFamilyCondition

Romantic A-Frame cabin in the woods
Indoor spacesKitchenView

Historic Schoolhouse c1866 + Pool + Lake + Hot tub
Indoor spacesFamilyView

Luxury Year-round Treehouse with private hot tub
Indoor spacesKitchenCondition

Loft Apartment on Tree-Lined Street in Falmouth
Indoor spacesKitchenWi-Fi

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool
Indoor spacesFamilyParking
Family- and pet-friendly home rentals

Studio Apartment in Freeport
FamilyKitchenWi-Fi

The Chickadee Tiny House
FamilyIndoor spacesComfort

Tree Yurt
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On the water Boathouse!
Indoor spacesKitchenOutdoor spaces

Modern stay Westbrook Maine
FamilyKitchenDecor

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Indoor spacesKitchenCleanliness

Yurt on Chebeague Island
Indoor spacesKitchenWalkability

Steep Falls Escape, river & falls just steps away
FamilyKitchenQuiet
Family-friendly home rentals with a pool

Attitash Retreat
FamilyIndoor spacesHospitality

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

Ski Chalet|Ping-Pong|Fire Pit|5 min -> Slopes
KitchenFamilySleep quality

3 Bears Glen, Across St. from Story Land, AC, pool
Indoor spacesKitchenAccess

Cozy Cottage with Ocean Views, Wells Maine
FamilyKitchenParking

Luxury Retreat In Back Cove | 10 Min to Downtown
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Maine Hacienda w/hot tub & seasonal pool
Indoor spacesFamilyParking

Gray Woodland Escape | Golf, Pool & Cinema
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When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $396 AUD | $373 AUD | $398 AUD | $334 AUD | $341 AUD | $439 AUD | $565 AUD | $555 AUD | $449 AUD | $396 AUD | $403 AUD | $396 AUD |
| 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 |
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- Pet-friendly rentals Windham
- Rentals with lake access Windham
- Rentals with beach access Windham
- Rentals with a fire pit Windham
- Rentals with a fireplace Windham
- Rentals with a patio Windham
- Rentals with outdoor seating Windham
- Waterfront rentals Windham
- Rentals with a kayak Windham
- House rentals Windham
- Rentals with a washing machine and dryer Windham
- Beachfront rentals Windham
- Cottage rentals Windham
- Family-friendly rentals Cumberland County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Long Sands Beach
- Popham Beach, Phippsburg
- Willard Beach
- York Harbor Beach
- Short Sands Beach
- Scarborough Beach
- Pemaquid Beach
- Footbridge Beach
- Pemaquid Point Lighthouse
- East End Beach
- Cape Neddick Beach
- Coastal Maine Botanical Gardens
- Gooch's Beach
- Popham Beach State Park
- Cranmore Mountain Resort
- King Pine Ski Area
- Hills Beach
- Conway Scenic Railroad
- Wolfe's Neck Woods State Park
- Crescent Beach State Park





