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Holiday rentals in Windham

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Windham

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

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Top guest favourite
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, 290 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.

Guest favourite
A welcoming sitting area features two comfortable chairs beside a small round table. Natural light floods through large windows, showcasing views of the serene lake. A television is mounted above a decorative fireplace, creating an inviting space for relaxation.
Home in Derry
4.92 out of 5 average rating, 504 reviews

Little Lake House, the Bungalow

Cozy up during your next trip to southern New Hampshire! The Little Lake house, situated right next to a serene lake, boasted luxury and spectacular water views. It's a perfect place for a peaceful escape or chance to experience the wide variety of seasonal New England activities from swimming and leaf peeping to ice fishing. The Little Lake house is a short drive to Canobie Lake Park and Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Top guest favourite
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.
Flat in Londonderry
4.97 out of 5 average rating, 143 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 favourite
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, 304 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.

Guest favourite
The exterior of a two-story building showcases a traditional design with white siding and dark blue shutters. A welcoming entrance is highlighted by a covered front porch and a set of stairs. Surrounding greenery adds to the inviting atmosphere.
Flat in Amesbury
4.78 out of 5 average rating, 259 reviews

Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Unwind in the modern 1BR 1Bath apt in the heart of downtown Amesbury, just a stone's throw away from tasty local restaurants and attractions. This charming oasis is perfect for leisure guests looking to explore nearby beaches and towns while also being close to hospitals and colleges, catering to traveling nurses and professionals. ✔ Comfortable King Bedroom ✔ Cozy Living Room ✔ Fully Equipped Kitchen ✔ Smart TV ✔ Workspace ✔ Washer/Dryer ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

Superhost
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.
Flat in Windham
4.88 out of 5 average rating, 336 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!

Top guest favourite
An open concept living area features modern furnishings, including a sofa with yellow and neutral accents. Large windows allow natural light to illuminate the space, which leads to a well-equipped kitchen and dining area in the background, enhancing the overall spacious feel.
Flat in Derry
4.93 out of 5 average rating, 273 reviews

Downtown Derry, A Modern 2-bedroom apt.

Cozy up during your next trip to southern NH! Built in 1910, the home has been completely renovated. The Riesling 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.

Superhost
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, 272 reviews

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

Top guest favourite
A two-story red house is viewed from the front, surrounded by greenery and trees. The property features a gravel driveway and a fenced backyard. Kayaks are seen by the water, which is just beyond the fence, providing a glimpse of the lake access.
Holiday home in Derry
4.96 out of 5 average rating, 173 reviews

Little Lake House-fishing, relaxation, 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.

Top guest favourite
Cottage in Windham
4.97 out of 5 average rating, 32 reviews

Ponder Point waterfront cottage at Cobbetts Pond

Come enjoy the breeze at this waterfront cottage located at Cobbetts Pond. This property has 2 bedrooms (1 king bed, 1 queen bed and a blow up mattress. Perfect for 4 people but up to 5 with a blow up mattress. We offer kayaks, an outdoor grill and a firepit. Although we are by the pond, the cottage is located minutes away from several hiking spots, dining, shopping, Canobie Lake Park, Tuscan Village etc. Agreement will have to be signed no exceptions.

Guest favourite
A clean studio condo is highlighted by natural light streaming through large sliding glass doors. A spacious bed occupies the room with a soft blue throw draped over it. A small dining table is positioned nearby, and a kitchenette is visible with modern amenities.
Apartment in Hampton Beach
4.86 out of 5 average rating, 107 reviews

Sunny Beach Studio Condo with Sunset View

Walk across the street for a day at the beach. Enjoy the beautiful, everchanging marsh views and sunset from your private deck in the evening. Clean, studio condo with great natural light and a well-equipped kitchen. Queen Bed with new mattress. Smart TV and wifi. Walking distance to restaurants and shops.

Guest favourite
A sandy area leads to the calm waters of Big Island Pond, framed by a tree providing shade. Small boats are docked nearby, and the serene landscape is complemented by clear blue skies and distant greenery.
Cottage in Derry
4.9 out of 5 average rating, 216 reviews

Little Red Lake House

My place is Located at Big Island Pond (with lake access), Manchester Airport & Boston Logan Airport are within an hour drive. Also local are The NH Seacoast, NH Lakes Region & White Mountains.. My place is good for couples and families (with kids). Follow me on Instagram Little_Red_Lake_House

Popular amenities for Windham holiday rentals

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$175 SGD$149 SGD$181 SGD$162 SGD$182 SGD$195 SGD$225 SGD$208 SGD$196 SGD$175 SGD$162 SGD$168 SGD
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Quick stats about holiday rentals in Windham

  • Total holiday rentals

    Explore 50 holiday rentals in Windham

  • Nightly prices starting at

    Windham holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Windham holiday rentals include wifi 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!