House vacation rentals in Windham

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Top-rated house rentals in Windham

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Guest favorite

The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.

Home in Naples

4.99 out of 5 average rating, 149 reviews

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.

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 North Deering

4.96 out of 5 average rating, 143 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew 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 eateries and breweries. 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, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Top guest favorite

A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.

Home in Windham

4.94 out of 5 average rating, 161 reviews

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.

Top guest favorite

A modern beach house is positioned along a serene shoreline, featuring large windows that reflect the colorful sunset. The exterior showcases a blend of natural materials and white accents, with a deck that offers expansive ocean views. Rocky shores frame the property, enhancing the coastal setting.

Home in Saco

5 out of 5 average rating, 192 reviews

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Guest favorite

A wooden staircase winds through lush greenery, leading down to a private dock on the tranquil lake. The water reflects the clear blue sky, framed by tall trees on either side, creating a serene outdoor setting.

Home in Standish

4.94 out of 5 average rating, 124 reviews

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.

Top guest favorite

The modern lakehouse structure is framed by tall trees, featuring large windows that provide ample natural light. A spacious deck is equipped with lounge chairs and picnic tables, while the lower level includes a hot tub. A clear lawn extends towards a serene backdrop.

Home in Oxford

5 out of 5 average rating, 214 reviews

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Guest favorite

The exterior of a red barn-style home is surrounded by lush greenery and colorful flower beds. A patio setup includes comfortable seating, a dining table with an umbrella, and a fire pit on a pebbled area, providing an inviting outdoor space.

Home in New Gloucester

4.97 out of 5 average rating, 115 reviews

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.

Top guest favorite

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

Home in Hollis

4.99 out of 5 average rating, 449 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Guest favorite

A bright corner of the cabin features a comfortable light-colored sectional sofa adorned with a decorative blanket. A wooden coffee table stands nearby, and natural light filters through large windows, highlighting the snowy landscape outside. A green potted plant adds a touch of nature to the space.

Home in Bridgton

4.98 out of 5 average rating, 132 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

Top guest favorite

A cozy bedroom features rustic wooden paneling and a sloped ceiling. A spacious bed with red and white bedding sits next to a wooden nightstand with a lamp. Additional storage baskets are arranged nearby, and light filters in through a window decorated with a sheer curtain.

Home in Cumberland

4.95 out of 5 average rating, 308 reviews

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.

Guest favorite

A modern kitchen with bright cabinetry features a central wooden table set for four. A simple vase with white flowers sits at the center. Light is seen coming through a nearby window, highlighting the retro blue refrigerator and clean countertops.

Home in Yarmouth

4.96 out of 5 average rating, 113 reviews

Close to Breweries, Outlets, and Portland Food!

Newly renovated and centrally located in charming Yarmouth Village! Enjoy a short walk to shops and restaurants, drive 15 minutes to Portland Old Port and renowned restaurants, or 5 minutes to Freeport Breweries/Outlets. Maine Beer Company, Mast Landing, LL Bean, Ottos, Royal River Grill all just minutes away. This is the perfect pit stop on your way to Acadia/ski mountains or to plan a day trip up the coast to Boothbay Harbor.

Superhost

A private balcony offers views of tranquil waters and nearby trees. A white chair is positioned against the railing, inviting relaxation while taking in the natural scenery. The landscape includes subtle reflections on the water's surface, enhancing the coastal surroundings.

Home in Littlejohn Island

4.93 out of 5 average rating, 133 reviews

Stone Isle. 8 acres next 2 little john preserve.

Nestled on 8 acres overlooking Casco Bay, the Stone Isle guest house has 2 bedrooms, 1 bathroom and amazing water views. The guest house includes an open plan layout with a full kitchen, living room (with sleeper sofa) and a dining table for 4. Last but not least the guest house is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!