
Holiday houses in Windham
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Top-rated holiday rentals in Windham
Guests agree: these stays 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.

Luxury Year-round Treehouse with private hot tub
Skyframe 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.

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.

Two bedroom duplex across st from crystal lake
Relax, have fun, spend quality time with friends and family right here at our quiet little place. Two bedrooms, three beds, one pull out couch, we can accommodate up to six guests. We have walking trails, firepit, and a barbecue area. The house sits across the street from crystal lake, with a boat launch 3/4 mile down the road with a parking area. An easy 20-minute drive to Portland. Supermarket, gas station, and restaurant less than five minutes away and ten minutes from Gray exit to 95.

Beautiful Home In Gorham Maine
Well appointed, bright and sunny apartment for two people in a quiet neighborhood. Large private back yard, formal gardens and pond, elevated deck, well stocked kitchen. 25 mins. to downtown Portland and the seacoast area. Minutes to local nature trails, swimming, kayaking, dining, supermarket & bakeries. ** NO PROFILE/REVIEWS? please provide a little info about whose coming, ie, name/age/occupation, reason of visit, etc, and any other info you wish to provide. Thank you!

Waterfront Cottage
The Waterfront Cottage sits directly on the shores of Snow Pond, 15 minutes from Colby College and downtown Waterville and 1/2 mile from the Snow Pond Center for the Arts. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have a private outdoor hot soaking tub and water view barrel sauna. Paradise!

The Roost - lovely one bedroom efficiency unit
Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

open concept Guest Suite in southern Maine
A short distance to many nature trails, Bradbury Mountain, state parks and the rocky coastline. This North Yarmouth guest suite is nestled between all the breweries and restaurants Portland has to offer as well as the famous outlet shopping in Freeport. We are located in a unique location where you are able to go from the rocky coast to the hiking trails all within 30 minutes. The guest suite is perfect for quiet lodging after a day of exploring or visiting.

The Retreat at Crystal Lake Farm
This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.

Rustic charm close to Portland
Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a group of 6 or a couple of 2 to unwind.

Spectacular River Retreat with Hiking Trails
Spectacular listing brought to you by seasoned Bath Superhosts! Enjoy sweeping views of the Kennebec River while cozying up by the fireplace. This modern art filled minimalist house sits on a bluff overlooking the Kennebec River and leads into Bath's peaceful Thorne Head Preserve, a vast network of trails that climb and hug the river's edge. It's just minutes away from downtown Bath, the historic and charming City of Ships.

Cottage on Black Brook Preserve
This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.
Popular amenities for Windham holiday rentals
Other great holiday rentals in Windham

Cabin Fever Reliever

Poet's Nook: Cozy and Private 1BR Apartment

The Cozy Cottage @ Loon Pond, Close to Event Venue

Lake Retreat in Windham, Maine — Sebago Lake

Designers Dream Home with Pool!

Cozy Maine Lakefront Paradise

Sebago Lake Winter House • Near Windham • Family

Christmas Tree Farm apartment
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $352 AUD | $282 AUD | $318 AUD | $311 AUD | $311 AUD | $371 AUD | $439 AUD | $436 AUD | $387 AUD | $352 AUD | $342 AUD | $352 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in Windham?
Windham has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cottage rentals in Windham?
Experience the best of Windham with our cottage rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Windham?
Yes! Work meets play with ease at over 80 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Windham have air conditioning?
Absolutely! We offer over 90 house rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Windham have a kitchen?
Absolutely! We offer over 20 cottage rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Windham have wifi?
Absolutely! We offer over 20 cottage rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Windham have free parking?
Absolutely! We offer over 30 cottage rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Windham

Total holiday rentals
Explore 180 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at $85 AUD per night before taxes and fees

Verified guest reviews
Over 8,200 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
170 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!
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- Rentals with beach access Windham
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- House rentals Windham
- Rentals with lake access Windham
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- Cottage rentals Windham
- Rentals with a patio Windham
- Rentals with outdoor seating Windham
- Waterfront rentals Windham
- Rentals with a fire pit Windham
- Family-friendly rentals Windham
- Beachfront rentals Windham
- Rentals with a kayak Windham
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Long Sands Beach
- Scarborough Beach
- Popham Beach, Phippsburg
- York Harbor Beach
- Popham Beach State Park
- Pemaquid Beach
- Cranmore Mountain Resort
- Willard Beach
- King Pine Ski Area
- Short Sands Beach
- Cape Neddick Beach
- Pemaquid Point Lighthouse
- Gooch's Beach
- East End Beach
- Diana's Baths
- Funtown Splashtown USA
- Crescent Beach State Park
- Coastal Maine Botanical Gardens
- Pleasant Mountain Ski Area
- Footbridge Beach




