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

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.

Annisquam Village Bunny Cottage
This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

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.

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!

Amazing Ocean View In-Law Apt.
Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

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.

Water front cabin-like guest suite on a quiet pond
Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Welcome to the Beach Escape! Seabrook, NH
Come stay in the BEACH ESCAPE! Walk 1,000 feet to Seabrook Beach in New Hampshire. After a day at the beach, come back to relax on the balcony overlooking the marsh, watch the sunsets and fireworks. The condo sleeps up to 3-4 people with a full sized bed and full sleeper sofa, TV, WiFi, kitchenette, central AC, and 2 chairs. Walk to amazing restaurants steps away. Our goal is for you to have an amazing time on the New Hampshire Seacoast! We have a check in time of 2PM.

Seasonal lake side cottage
Cottage comes with the use of two kayak's, a canoe, two stand up paddle boards, hammock and outside fire place to roast s'mores. (Please do not use fireplace until dusk). Refrigerator & freezer, microwave, keurig, toaster, basic pots and pans, outside grill,a clean lake with swimming area. Tv/DVD player & DVD’s(no cable), WiFi. We supply towels,linens & beach towels. Friendly neighbors on either side of cottage. A perfect relaxing, unplugged weekend getaway.

Lakefront getaway w s’mores+firepit by pats peak
15 minutes to Pats Peak. Adorable, tiny New England towns! Small family restaurants 10 minutes. The wall of windows will encourage you to relax or play on the frozen lake and make s”mores @ the fire pit (wool blankets provided.). Cozy living room stocked with boards games, smart TV & DVDs. WiFi, full kitchen and full bath. Upgraded experience like linen sheets, echo home manual, espresso maker and satin pillow cases. 3 person max, no children, no smoking.

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.

Halibut Point State Park. Nature Lovers Retreat
"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.
Popular amenities for Windham vacation rentals
Other great vacation rentals in Windham

R. Hill Tree Top Studio!

The Rustic Retreat

A Spacious Modern Elegant Ranch (whole house)

Ponder Point waterfront cottage at Cobbetts Pond

Lake Cottage in Windham

Quaint Cottage near Cobbetts Pond

Lakefront! Johnson Point Cottages-“Summer Breeze”

Power Terrace Cozy
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 117 | € 99 | € 120 | € 108 | € 121 | € 130 | € 141 | € 143 | € 128 | € 116 | € 108 | € 112 |
| 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 $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 € 35 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!
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- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Ogunquit Beach
- Wells Beach
- Revere Beach
- Boston Seaport
- Boston University
- Pats Peak Ski Area
- Freedom Trail
- New England Aquarium
- MIT Museum
- Long Sands Beach
- Boston Convention and Exhibition Center
- Gillette Stadium
- Monadnock State Park
- Canobie Lake Park
- Crane Beach
- York Harbor Beach
- Quincy Market
- Museum of Fine Arts
- North Hampton Beach




