Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Top guest favorite
A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.
Cabin in South Berwick
5 out of 5 average rating, 287 reviews

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

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, 307 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
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, 158 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.

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, 316 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
4.94 out of 5 average rating, 126 reviews

Large Private Guest House with Lake Views in 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) with additional queen futon. Unit is clean & comfortable with 2 smart tv's, wifi, Keurig, microwave, minifridge/freezer. Explore the lake using 2 available kayaks. Two public beaches nearby. Parking for 3 cars. Minutes from Canobie Lake Park & Tuscan Village. 5 Wedding venues w/in 5 miles. Short drive to NH seacoast, white mountains &foliage.

Top guest favorite
The exterior of the house features a spacious deck with white railings and steps leading to the ground level. The lower terrace is adorned with decorative pots and greenery, while a gravel pathway provides access to the entryway.
Apartment in Plum Island
4.98 out of 5 average rating, 417 reviews

My Dream house with views of the marsh and sunset

Our rental space has two bedrooms, living room, full bath and a mini kitchen. There is a full deck across the front of the house and a large patio off the bedrooms which is accessed though the sliders in each bedroom. This is all private space for our guests. The views from the front deck are of the great marsh along with the beautiful sunsets. With the Two bedrooms one with a queen size bed and the other with full size bed the house can have 2 to 4 people depending on sleeping arrangements.

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
4.88 out of 5 average rating, 354 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 exterior of the carriage house features a distinctive angled roof and white clapboard siding. A vibrant red door stands at the entrance, accompanied by a small seating area with black furniture and orange accents. The surrounding landscape includes greenery and a children's swing set.
Place to stay in Windham
4.95 out of 5 average rating, 37 reviews

Adorable Carriage House with history & charm

Enjoy the natural beauty surrounding this historic getaway. This unique Carriage house built in early 1900’s, sits on the same property as the Chic Austin Estate. The Estate was built in 1743 & has housed many stars such as Frank Sinatra, Betty Davis & Houdini. The newly renovated carriage house is minutes from Cobbetts Pond, hiking, skiing, Tuscan Village, State parks, biking, Canobie Lake & shopping. Create a romantic getaway with someone special or create memories with your family.

Top guest favorite
An open-concept living area is highlighted by hardwood floors and a vaulted ceiling. A maintenance-free reef tank with ambient lighting is displayed on the wall. Modern seating options include a sectional sofa and chairs arranged around a coffee table, with large windows providing natural light.
Apartment in Westford
4.95 out of 5 average rating, 134 reviews

Large One Bedroom Apartment

1,100 square feet, completely renovated, 1 bedroom with a walk-in closet. Large bathroom with two sinks and walk-in shower. Open concept living, dining and kitchen area with vaulted ceiling. Hardwood floors throughout. Central air. Apartment is connected to a main house but with no interior access between house and apartment whatsoever. (No interior connecting doors at all) It has its own private driveway and side yard. Reef tank will no longer be in the apartment after May 20th.

Top guest favorite
An outdoor seating area is set on a patterned rug, featuring a black table surrounded by four red chairs. A grill is positioned nearby, and a wooden deck leads towards the water, framed by a black fence and trees that provide shade.
Vacation home in Derry
4.96 out of 5 average rating, 195 reviews

Little Lake House- Swimming, Fishing, Waterfront

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 favorite
A rustic cabin features a fire pit surrounded by multiple chairs, inviting outdoor gatherings. The wooden structure showcases earthy tones, nestled among trees with colorful foliage. Tiki torches are positioned nearby, enhancing the cozy atmosphere for evening relaxation.
Cabin in Windham
4.9 out of 5 average rating, 159 reviews

Little Lake, Big Fish - Fire Pit & Pvt Beach

@DiamondHomeCollection on Insta Please read Other Details To Note 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 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. And spring

Guest favorite
Two individuals are seated in white chairs on a stone patio, positioned around a crackling fire. The cottage is visible in the background, showcasing large windows and a rustic wooden deck. Lush greenery frames the area, contributing to the natural surroundings.
Cottage in Epsom
4.96 out of 5 average rating, 230 reviews

Smokey Pines Camp

Cozy, private cottage on the Suncook River. Great for kayaking, fishing, tubing, and swimming. Very private with meadow, outdoor picnic areas, and fire pits. Within walking distance to Bear Brook State Park. 40-minute drive to Portsmouth, Manchester, and Lake Winnepasakee. One hour away from the New Hampshire White Mountains and Boston.

Popular amenities for Windham vacation rentals

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR2,323 ZARR1,979 ZARR2,392 ZARR2,151 ZARR2,409 ZARR2,581 ZARR2,805 ZARR2,856 ZARR2,547 ZARR2,306 ZARR2,151 ZARR2,237 ZAR
Avg. temp-2°C-1°C3°C9°C15°C20°C23°C22°C18°C11°C6°C1°C

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 house rentals in Windham?

    Windham has more than 10 family-friendly house rentals. 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 $130 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 R688 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 3,670 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!