
Holiday rentals in Windham
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Top-rated holiday rentals in Windham
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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.

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.

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.

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.

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!

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!

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.

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!

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.

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.

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.

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
Other great holiday rentals in Windham

The Carriage House, A Retro Loft

Little Lake, Big Fish - Fire Pit & Pvt Beach

Extra large 1 bedroom apartment

The Rustic Retreat

modern Tudor in beautiful Salem nh

Idyllic Small-Town Stay (2 Bed)

Althea’s Retreat

Spacious Private Loft on Main Street (3rd FL)
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 | 
| Avg. temp | -2°C | -1°C | 3°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 6°C | 1°C | 
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! 
Destinations to explore
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- Hampton Beach
- Ogunquit Beach
- Fenway Park
- Boston Common
- Wells Beach
- TD Garden
- Harvard University
- Revere Beach
- Lynn Beach
- York Harbor Beach
- Monadnock State Park
- New England Aquarium
- Long Sands Beach
- Good Harbor Beach
- Freedom Trail
- Canobie Lake Park
- MIT Museum
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Quincy Market
- Rye North Beach
- North Hampton Beach
- Prudential Center
