
Holiday rentals in Windham
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Top-rated holiday rentals in Windham
Guests agree: these stays are highly rated for location, cleanliness and more.

Sanctum by the Lake
Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

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.

Peaceful Mill with Waterfall - Home Away From Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

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.

Extra large 1 bedroom apartment
This spacious place to stay is perfect for work or vacation! Our huge bedroom basically has a 2nd living room in it complete with a pull out bed under the sofa for extra sleeping room and a desk for working. The kitchen is complete with a brand new stove, full size refrigerator, dishwasher and microwave. The living room has a dining table for 3 and another pull out couch suitable for sleeping. In unit washer dryer and a shower you dream of! 8 min drive to Tuscan Village, 8 mins to Canobie Lake!

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.

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.

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.

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

Accessory Apt on Wooded Property
Forget your worries in this spacious and serene space. Guest House/Over Garage Apartment tucked away on 6 acres. Centrally locataed in the seacoast region of New Hampshire. Close to mountains, beaches, hiking trails, lakes, & more. 15 minutes to Exeter, 30 minutes to North Hampton/Hampton Beach, 35 minutes to Southern Maine and Portsmouth, NH, 40 minutes to Manchester Boston Regional Airport, and 1 hour to Downtown Boston yet still tucked away in your own private retreat in the woods.

Newly renovated, spacious, clean, 3 bedroom home.
Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Romantic Mirror cabin in the woods
Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.
Popular amenities for Windham holiday rentals
Other great holiday rentals in Windham

The Carriage House, A Retro Loft

Hillside Hideaway – Relax & Recharge in Vanprasth

Willow Falls Home ~Hot tub & Waterfront

Waterfront Lake House on Cobbetts Pond!

modern Tudor in beautiful Salem nh

Quaint mountain top Bungalow

Cozy 3 bedroom cottage with a short walk to beach

Waterfront 2 Bedroom on private cove in Salem NH.
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹12,405 | ₹11,928 | ₹11,928 | ₹11,928 | ₹13,359 | ₹14,314 | ₹15,554 | ₹15,840 | ₹14,123 | ₹12,787 | ₹11,928 | ₹12,405 |
| 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 |
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 $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
Do cottage rentals in Windham have wifi?
Absolutely! We offer over 10 cottage 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 holiday rentals in Windham

Total holiday rentals
Explore 50 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at ₹3,817 per night before taxes and fees

Verified guest reviews
Over 3,750 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 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!
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Ogunquit Beach
- Wells Beach
- New England Aquarium
- Revere Beach
- Boston Seaport
- Northeastern University
- Boston University
- Gillette Stadium
- Freedom Trail
- Boston Convention and Exhibition Center
- Long Sands Beach
- MIT Museum
- Pats Peak Ski Area
- Monadnock State Park
- Canobie Lake Park
- Crane Beach
- York Harbor Beach
- Quincy Market
- Roxbury Crossing Station





