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Windham vacation rentals

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Top-rated vacation rentals in Windham

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

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Guest suite in Windham

4.99 out of 5 average rating, 259 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.

Rental unit in Londonderry

4.97 out of 5 average rating, 113 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.

Home in Windham

4.93 out of 5 average rating, 280 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.

Home in Derry

4.79 out of 5 average rating, 109 reviews

Beautiful Garden Studio apartment

Welcome to my Beautiful Garden studio apartment. This is a nice and affordable place to enjoy alone or with your loved one. The studio is on the smaller side (Nice, cozy, tiny home size), it has everything you need. Everything is new and updated. The most beautiful thing about the apartment is how efficient and simple it is! Derry, NH is just 45 mins north of Boston W/O traffic. 15 mins from Manchester, NH. 40 mins from Portsmouth NH. Derry is amazing for getaways. Plenty of lakes and trails!

Guesthouse in Amesbury

4.95 out of 5 average rating, 113 reviews

Two Penny Loft at Amesbury Farmhouse - Guest Suite

This cozy 2 story guest suite w/separate entrance and deck, is part of a large 200 year old Amesbury farmhouse set on a peaceful 3 acre lot. The first floor contains a comfortable living/dining area, along with small charming bathroom. Upstairs is a large bedroom with vaulted ceiling, skylights, king-sized bed and sitting area. Amesbury is steeped in history and guests will be close to amazing breweries, restaurants, historical sites, shops, galleries, walking trails, lakes, beaches and more!

Rental unit in Windham

4.88 out of 5 average rating, 289 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.

Rental unit in Windham

4.86 out of 5 average rating, 198 reviews

The Estate Escape with Hottub

The apartment is new with high-end finishes, but there is still a storage container outside in the front of the house. (See pictures.) Cozy up during your next trip to southern New Hampshire! The Estate Escape is a perfect place for a peaceful escape with its own hot tub. The Estate Escape is minutes away from Canobie Lake Park, Castleton, and La Belle Winery. It is a short drive to Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Loft in Derry

4.98 out of 5 average rating, 627 reviews

Comfort and Convenience in a Private Studio

*Please note that we are located on a main road * Welcome! No matter what brings you to Derry, we guarantee your comfort and convenience. Our 400 square foot studio boasts privacy, style, and value. The apartment is simple, modern, and warm. Coffee, tea, and treats are provided; we want you to feel like you are home away from home. Curl up for your favorite show with Hulu Live and enjoy your morning coffee out on the balcony. The space accommodates 2 comfortably (with room for up to 4).

Guest suite in Merrimack

4.99 out of 5 average rating, 189 reviews

Guest suite with king bed and private entrance

Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

Guest suite in Hollis

4.98 out of 5 average rating, 138 reviews

Pine Estate - Private suite

Welcome to our spacious guesthouse located - 2 miles from Nashua - 5 minutes drive to the highway - 40 minutes to Boston and minutes from Hollis. Hollis is an active farming community offering beautiful orchards, nature paths, art studios and a winery. Beautiful private yard with a large patio where you can relax and enjoy nature at its best. Our place is ideal for a weekend get-away or business travelers. Please note there will be no exception to the no pets policy.

Vacation home in Derry

4.97 out of 5 average rating, 117 reviews

Little Lake House-Kayaking, Swimming & more

Welcome to our home away from home. This cozy lake get away just minutes over the border from Massachusetts is the perfect place to connect with friends and family. Enjoy days out on the water which is right outside your back door! Or nights at the fire pit enjoying the stars. We have wifi, tv w/ streaming services, laundry, a/c & heat, and kayaks to make your stay as comfortable and fun as possible. We're family friendly and have a crib for infant/baby.

Guest suite in Loudon

4.95 out of 5 average rating, 260 reviews

Private In-Law Apartment With Views and Hot Tub

RENOVATED SEPTEMBER 2023! Private 1bed, 1 bath in-law apartment with dedicated entrance and no shared spaces, moments from historic downtown Concord NH. Enjoy the sunset behind Mt. Kearsage while sitting around the fire pit overlooking the surrounding valley. Under 40 minutes to Gunstock Mountain and Pats Peak, and less than one hour to Crotched and Ragged Mountain. 30 minutes to Lake Winnisquam and Lake Winnepesauke. Main Home also available.

Vacation rentals for every style

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Popular amenities for Windham vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Windham's top sights

Canobie Lake Park60 locals recommend

The Mall at Rockingham Park20 locals recommend

The Common Man11 locals recommend

Tuscan Kitchen11 locals recommend

Tuscan Village Marketplace8 locals recommend

Enterprise Rent-A-Car8 locals recommend

Other great vacation rentals in Windham

Guest suite in Milford

5 out of 5 average rating, 83 reviews

New England Village Luxury Studio

Rental unit in Londonderry

5 out of 5 average rating, 11 reviews

Cozy In-Law Guest Suite— 2 Miles to Highway

Guesthouse in Salem

4.93 out of 5 average rating, 72 reviews

Large Private Guest House with Lake Views in NH

Rental unit in Salem

4.88 out of 5 average rating, 80 reviews

Chic Salem, NH Studio Apartment

Guesthouse in Westford

4.97 out of 5 average rating, 98 reviews

Detached Waterfront Guest House

Guesthouse in Windham

4.85 out of 5 average rating, 79 reviews

Private Guest House

Guesthouse in Lowell

5 out of 5 average rating, 12 reviews

Private guest house

Rental unit in Lawrence

4.92 out of 5 average rating, 39 reviews

Beautiful and Cozy Private Studio in Lawrence MA

Quick stats about vacation rentals in Windham

Total rentals
40 properties
Total number of reviews
3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

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 Windham Depot, and over 20 vacation rentals in West Windham.
Are there pet-friendly vacation rentals in Windham?
Four-legged friends are welcome in Windham. Choose from more than 10 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 20 vacation rentals in Windham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in cottage rentals in Windham?
Experience the best of Windham with our cottage rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly cottage rentals in Windham?
Windham has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Windham have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet 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.
Do cottage rentals in Windham have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Windham. Enjoy a tailored experience with all the comforts you desire.

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