Vacation rentals in Windham

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Top-rated vacation rentals in Windham

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious home sits on a manicured lot, featuring a well-kept garden and an expansive driveway. The two-story structure boasts large windows and a welcoming entrance, with outdoor lighting enhancing its features during twilight. The attached garages are visible on the right.
Guest suite in Windham
4.99 out of 5 average rating, 317 reviews

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

Top guest favorite
Cabin in Stoddard
4.98 out of 5 average rating, 240 reviews

Cozy Comfort on 250 Acre Private Estate

If you’re looking for serenity, peace and quiet, you've found it, amidst a 250 acre private estate. On a lake at the end of a mile long driveway (well plowed in the winter) Is Snowshoe Cabin. Built in 1929 as the garage for "Lakefalls Lodge, it's been completed renovated into a luxurious, cozy home with modern amenities. Guests rave about "views of the snowy pond while you’re warm inside" from heated floors and a wood burning stove with free firewood. Spikes provided for wonderful winter walks.

Top guest favorite
The exterior of the home and attached apartment is shown, featuring a light-colored facade with dark trim. A paved driveway leads to a two-car garage, surrounded by landscaping of shrubs and trees. An American flag is displayed, providing a welcoming touch.
Apartment in Londonderry
4.97 out of 5 average rating, 164 reviews

The Birch Suite: Large, Cozy NH Themed Apartment

Our home and attached apartment is tucked away in a quiet neighborhood in southern NH, just minutes from major N/S highway Route 93. We are thrilled to offer our New Hampshire-themed apartment to individuals, couples and families. Each room is decorated to represent the most interesting aspects of our state: the purple lilac bathroom, the maple bedroom, the white birch living room and a large second bedroom/playroom we call "the state room" - a fun, educational room of all things New Hampshire.

Top guest favorite
A quaint cabin is positioned among trees, softly lit at night. An illuminated entrance is framed by colorful pots and surrounded by a cozy seating area with an Adirondack chair. Flickering firelight adds warmth to the inviting outdoor space.
Cabin in Littleton
4.99 out of 5 average rating, 219 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Guest favorite
An aerial view showcases a spacious property surrounded by lush trees, featuring a large private tennis court and half-basketball court. The well-manicured grounds are complemented by additional outdoor areas, highlighting a serene and inviting environment.
Home in Windham
4.93 out of 5 average rating, 321 reviews

One Level 2 bedroom suite on private cul-de-sac

Welcome to The Sama's Airbnb. Windham was recently named the #1 town in the Granite State. Here, you will enjoy a complete newly renovated private one level 2 bedroom suite complete with full kitchen, cozy living room, 40 inch LED TV with all channels, wifi, washer and dryer, new tennis court, 1/2 basketball court and pickleball, beautifully landscaped grounds on a private cul de sac yet close to Boston, beaches, mountains, shopping, great restaurants, Searles Castle, Canobie, & Tuscan Village.

Top guest favorite
A serene view of the calm lake is presented, framed by trees and surrounding greenery. The water reflects the clear sky, while homes are visible along the bank, creating a peaceful landscape perfect for relaxation.
Guesthouse in Salem
4.93 out of 5 average rating, 135 reviews

Lake Front Private Guest House in So. NH

Just 36 miles north of Boston/Logan Airport. Enjoy lake views from this above garage private entrance guest house. Two private bedrooms (1 queen/1 full) w/additional queen futon. Unit is clean & comfortable with 2 smart tv's, wifi, Keurig, microwave, minifridge/freezer. Explore lake using 2 available kayaks. Two public beaches nearby. Parking for 3 cars. Minutes from Canobie Lake Park, Tuscan Village & 5 popular wedding venues. Short drive to So Maine, NH seacoast, white mountains & foliage.

Guest favorite
A modern kitchen is presented with white cabinets and stainless steel appliances, including a refrigerator and oven. Granite countertops provide ample workspace, with a sink beneath a window. Natural light fills the area, enhancing the open and inviting atmosphere.
Apartment in Windham
4.89 out of 5 average rating, 361 reviews

The Cozy Corner Apartment

Cozy up during your next trip to the southern New Hampshire area! The Cozy Corner is a combination of style and comfort in so many ways from the double windows and sliding glass doors that flood the space with light to the airy and peaceful design that makes it feel like home. The Cozy Corner is a short drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston and NH Seacoast, close to Lakes Region, White mountains, and great skiing spots. 10 minutes from major shopping centers!

Guest favorite
The dining area features a wooden table surrounded by four high-backed chairs. A large piece of artwork is displayed on the wall, and a potted plant adds a touch of greenery. The open kitchen is visible in the background, equipped with modern appliances.
Apartment in Derry
4.87 out of 5 average rating, 127 reviews

3 Bedroom Apartment in Downtown Derry

Cozy up during your next trip to southern NH! Built in 1910, this apartment has been completely renovated. Meadowview is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Guest favorite
The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.
Farm stay in North Andover
4.95 out of 5 average rating, 296 reviews

Winery Studio w/ Private Hot Tub & Wine Tasting

Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

Top guest favorite
A serene lakeside view captures a vibrant sunset with the sun partially descending behind distant hills. A lone fisherman in a boat is visible on the water, while a wooden deck features seating arrangements surrounded by lush plants.
Guest suite in Tyngsborough
4.98 out of 5 average rating, 269 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake, the upstairs suite has a panoramic view from the bedroom, a private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room - it feels like an apartment, but no kitchen. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants, a casino, or tax-free shopping. We are one hour from Boston.

Superhost
A sandy beach area is visible, bordered by lush green trees, leading to a tranquil lake. The calm water reflects the clear blue sky, while scattered boats are moored along the shoreline. Sunlight filters through the leaves, creating dappled shadows on the sand.
Cottage in Windham
4.83 out of 5 average rating, 52 reviews

Quaint Cobbetts Pond Cottage with Pond Views

A cute, clean & cozy, one bedroom cottage on Cobbetts Pond in Windham NH. The cottage is a few feet from a shaded, private community beach and you can view the sunrises each morning over the pond. The cottage is well appointed and the entire place is yours to enjoy There are tons of hiking trails nearby & the lake is clear and perfect for swimming and canoeing in the provided canoe! We are less than an hour drive from Boston & the beach. House was built in 1934

Superhost
An outdoor seating area features four blue chairs arranged around a fire pit, with cushions providing comfort. A red umbrella shades a nearby table for four, while a propane grill sits ready for use. A charming cottage is visible in the background, surrounded by trees.
Cabin in Windham
4.87 out of 5 average rating, 99 reviews

Big Fish, Little Lake - Fire Pit & Pvt Beach

Please read Other Details to Note @DiamondHomeCollection on Insta Come Fish & Kayak here! Our area is full of life and peace. Wake up to the loons early in the morning and go to bed listening to the owls. Watch the turkeys or fox cross the yard. Our homes are from the 1920's, we keep them alive and for the souls who love old homes. 45 minutes to the ski destinations ocean, lakes region, and hiking. Not waterfront, we own shares of waterfront.

Popular amenities for Windham vacation rentals

When is the best time to visit Windham?

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Avg. priceﺩ.ﺇ 477ﺩ.ﺇ 459ﺩ.ﺇ 459ﺩ.ﺇ 459ﺩ.ﺇ 514ﺩ.ﺇ 551ﺩ.ﺇ 599ﺩ.ﺇ 610ﺩ.ﺇ 544ﺩ.ﺇ 492ﺩ.ﺇ 459ﺩ.ﺇ 477
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Frequently Asked Questions

  • Where should I stay in Windham?

    Make yourself at home in Windham by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in West Windham, and over 20 vacation rentals in Windham Depot.

  • Are there pet-friendly vacation rentals in Windham?

    Four-legged friends are welcome in Windham. Choose from more than 20 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 30 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Windham?

    Windham has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Windham?

    Experience the best of Windham with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Windham have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windham have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Windham have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Windham. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Windham

  • Total vacation rentals

    Explore 50 vacation rentals in Windham

  • Nightly prices starting at

    Windham vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

  • Verified guest reviews

    Over 3,750 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Windham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Windham rentals

  • 4.8 Average rating

    Windham stays are highly rated by guests—averaging 4.8 out of 5!