House vacation rentals in Windham

4.95 out of 5 average rating, 268 reviews

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.

ValueLocationAir conditioning

4.89 out of 5 average rating, 641 reviews

Home in Westbrook

Cozy Maine Cottage • Near Jetport & Coast

Cozy Cottage Retreat w/ Loft near Portland Welcome to your Maine escape. Reno barn offers a warm, cottage-inspired atmosphere with character, an open loft, and inviting spaces for rest and connection. Located mins from the airport and within walking distance to Allagash Brewing Company and other local favorites. A quick drive to downtown Portland, beaches, lighthouses, and live music. End your evenings on the private back deck — wine in hand, stars overhead, and nothing but quiet around you.

FamilyLocationDecor

4.97 out of 5 average rating, 174 reviews

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

ValueFamilyPool

5.0 out of 5 average rating, 245 reviews

Home in Oxford

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.

LocationValueDecor

4.97 out of 5 average rating, 197 reviews

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!

FamilyLocationSleep quality

Superhost

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.

4.88 out of 5 average rating, 106 reviews

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.

FamilyValueAccuracy

A private dock extends into the calm waters of Highland Lake, surrounded by lush greenery along the shoreline. Clear blue skies reflect on the water's surface, creating a serene environment for outdoor activities.

4.98 out of 5 average rating, 43 reviews

Lakefront, Dock, Kayaks, & SUPs-Windham Wind Down

Welcome to Windham Wind Down, your peaceful getaway in Windham, Maine! As you step into this charming lake house, you’ll be greeted by beautiful views and the fresh scent of the surrounding pines. Whether you're here for adventure or relaxation, this home provides everything you need for an unforgettable stay including private lake access. Spend your days kayaking, paddle boarding, or fishing on the lake off of the private dock, and unwind by the fire pit in the evening.

FamilyLocationLong stay

A spacious backyard features a firepit surrounded by six blue Adirondack chairs, creating a cozy gathering area. The well-maintained lawn is bordered by trees, and the home is visible in the background with warm lighting illuminating its deck and windows.

5.0 out of 5 average rating, 66 reviews

Maine Vacation Home on the Water

Create memories with family and friends at this well loved waterfront home with plenty of fun to be had whether you’re spending the day floating down the lazy ‘river’, swimming at the small association beach, kayaking on the pond or enjoying meals and games inside. Downtown Windham is minutes away (there is some traffic noise at the property) and has nice shopping and sweet restaurants while Portland is just 16 miles with everything Maine’s largest city has to offer.

FamilyLocationAmenities

4.97 out of 5 average rating, 203 reviews

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

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.

LocationFamilyHospitality

4.94 out of 5 average rating, 140 reviews

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

Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), summer fun (beaches & watersports galore), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make lasting memories!

FamilyValueHospitality

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.

4.96 out of 5 average rating, 202 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 Lakeside Tavern, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

LocationValueAccuracy

4.91 out of 5 average rating, 104 reviews

The exterior of a historic farmhouse is presented, featuring two stories with white trim around multiple windows. A central front door is flanked by light fixtures, and landscaped greenery, including hostas, surrounds the entrance. A well-maintained lawn adds to the inviting aspect of the property.

Home in Falmouth

Wild Rose Farm -Three Queen Suites

Wild Rose Farm is a historic, antique farmhouse in a suburban setting close to Route 1 in Falmouth. The main house has 3 queen suites with additional beds as needed. This farmhouse is perfect for a family or friend getaway. This listing is for the whole farmhouse + barn. Small events may be allowed with prior approval. Please inquire FMI

ValueLocationAmenities

Popular amenities for Windham house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5.0 out of 5 average rating, 103 reviews

A heated pool is set within a stone patio, surrounded by lush greenery. Two lounge chairs are positioned nearby, while modern heating units stand along the patio's edge. The pool's clear water reflects the surrounding area, offering a serene outdoor retreat.

Home in Ogunquit

Ogunquit Village 5 BDR, Heated Pool, Walk to Beach

FamilyValueAccuracy

4.83 out of 5 average rating, 179 reviews

Home in Kennebunk

Beach House w/ Heated Pool · Fire Pit · Kennebunk

ValueLocationKitchen

4.84 out of 5 average rating, 126 reviews

A two-story home is presented, featuring a yellow exterior and dark blue shutters. A welcoming front porch is adorned with decorative elements. Lush green grass and various shrubs frame the entrance, while a driveway leads to a garage on the left side.

Home in Portland

There's No Place Like Home

LocationValueComfort

Home in Old Orchard Beach

A serene community pool is surrounded by a spacious deck with lounge chairs for relaxation. Tall trees in the background provide a natural setting, while neighboring homes are visible, enhancing the sense of community.

Faith Lane with community pool

LocationFamilyAccuracy

4.96 out of 5 average rating, 123 reviews

4.98 out of 5 average rating, 132 reviews

Home in Bartlett

River Access|Gas stove|Min to N. Conway, Attitash

FamilyLocationHiking

4.96 out of 5 average rating, 71 reviews

Unique Church Stay • Sebago Lake • Pool • Fire Pit

LocationFamilySleep quality

4.98 out of 5 average rating, 58 reviews

A classic beach house is situated amidst lush greenery, featuring a charming wraparound porch. The two-story structure is accentuated by large windows and a balcony above. A clear blue sky complements the inviting landscape, creating a serene setting just steps from the beach.

Home in Kennebunkport

Lovely Beach house in GRB - Heated pool!

FamilyLocationLayout

5.0 out of 5 average rating, 34 reviews

A single-story home features a welcoming façade with a mix of stone and wooden elements. A spacious stone patio surrounds a circular fire pit, inviting outdoor gatherings. Lush greenery encircles the property, complementing the home’s charming exterior and large windows that provide ample natural light.

Home in Biddeford

The Hurkle Durkle House

FamilyLocationAmenities

Weekly house rentals

A circular fire pit is surrounded by several black Adirondack chairs, set on a lush green lawn. The tranquil surface of the lake reflects the blue sky and fluffy clouds, while trees in varying shades of green line the opposite shore.

4.97 out of 5 average rating, 38 reviews

Lakefront | Dock + Fire Pit Near Sebago & Portland

LocationFamilyTV

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.

4.97 out of 5 average rating, 89 reviews

Lakehouse on Highland Lake

LocationFamilySkiing

5.0 out of 5 average rating, 21 reviews

Serene Modern Lakefront Escape l 20 min Portland

LocationFamilyOutdoor spaces

4.98 out of 5 average rating, 89 reviews

The kitchen features a spacious island with seating for four and a modern design. Recessed lighting complements bright fixtures above the island. Countertops are finished in dark stone, and stainless steel appliances are visible, enhancing the inviting kitchen space.

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

FamilyValueAmenities

5.0 out of 5 average rating, 24 reviews

A vibrant garden features clusters of purple flowers in full bloom, enhancing the greenery of the lawn. A gazebo is visible in the background, alongside the tranquil lake, which reflects the clear blue sky. Tall trees provide shade, adding to the serene environment.

Home in Gray

Coveside on Little Sebago

LocationFamilyBathroom

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.

4.98 out of 5 average rating, 60 reviews

Cozy Camp on the lake

ValueLocationComfort

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.

4.95 out of 5 average rating, 61 reviews

Rise & Shine - Breathtaking Sebago Lake view

LocationValueBeach

Superhost

5.0 out of 5 average rating, 3 reviews

Lakeside Retreat | Lake Access | Grill & Fire Pit

FamilyWalkabilityBeach

Private house rentals

The cottage is illuminated softly against the night sky, showcasing a large front deck with rocking chairs. The main entrance is framed by bright windows, adding warmth to the exterior. Surrounding trees create a serene atmosphere, enhancing the peaceful setting.

4.93 out of 5 average rating, 98 reviews

Sebago Lake, ME *Lakeside*Hot Tub* just renovated

LocationValueCondition

The exterior of a new lake house presents a modern design with light green siding and large windows on either side of a central double door entrance. A gravel pathway leads to the front door, surrounded by a grassy area and tree line in the background.

4.93 out of 5 average rating, 60 reviews

The Lake House

LocationFamilyBeach

4.97 out of 5 average rating, 74 reviews

A modern cabin nestled among tall trees features a spacious deck with cushioned loungers for relaxation. Kayaks and a canoe are positioned nearby, highlighting the outdoor recreational opportunities. The cabin structure showcases large windows that invite natural light into the interior.

Home in Falmouth

Cozy Lakefront Cabin Near Portland

LocationValuePets

5.0 out of 5 average rating, 45 reviews

A serene patio area is set near the lake, featuring a round table surrounded by four cushioned chairs beneath a large umbrella. Lush greenery frames the view, complementing the gentle waters of the lake in the background.

Home in Gray

The Lazy Hummingbird - Little Sebago Home w/ Sauna

LocationFamilyQuiet

5.0 out of 5 average rating, 15 reviews

Home in Raymond

Beautiful Lakefront View, on Sebago Lake

FamilyLocationBathroom

A serene lakefront view showcases a newly renovated home nestled among trees. The spacious yard includes seating areas with chairs, and a rocky shoreline borders the clear water. Sunlight filters through the trees, highlighting the peaceful setting ideal for outdoor relaxation.

5.0 out of 5 average rating, 35 reviews

Arthur's Place • Sebago Lakefront • Near Windham

FamilyLocationAccess

A modern two-story house features an architecturally striking facade with large glass windows. The spacious deck is surrounded by black railings, providing ample room for outdoor seating. Lush green trees frame the property, while a gravel driveway is visible in the foreground.

4.96 out of 5 average rating, 28 reviews

Sebago Lake Beach Paradise

FamilyLocationGrill