Vacation rentals in Windham

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Popular amenities for Windham vacation rentals

Other great vacation rentals in Windham

Apartment in South Londonderry
4.92 out of 5 average rating, 367 reviews

Cozy Suite in a Historic Building Near Ski Resorts

DylanRating, 5 stars1 week ago
Staying at Jason’s cozy suite in Londonderry was an absolute treat. The space was warm, clean, and thoughtfully arranged, perfect for unwinding after a day of exploring the Green Mountains. Everything from the comfortable bed to the charming rustic touches made it feel like a true Vermont escape. Jason was a great host! Very responsive, welcoming, and respectful of privacy. The location was ideal: close to local trails, ski spots, and great small-town food, but still tucked away enough to enjoy some real quiet. Highly recommend for anyone looking to slow down and soak in the calm beauty of Vermont. I’d definitely stay again.
Guest favorite
Tiny home in Chester
4.93 out of 5 average rating, 40 reviews

Sage House at Camp Greenwood Vermont with Sauna

PatrickRating, 5 stars5 days ago
Was exactly like the photos. A beautiful home and beautiful town.
Top guest favorite
Tiny home in Jamaica
5 out of 5 average rating, 11 reviews

Stratton; 5 min. Pikes Falls, 1 min. Fire pit

RitaRating, 5 stars7 months ago
What a perfect tiny home and what a perfect stay! Very quiet rural location, the tiny home is pristine and cozy, decorated with love. Very good heating system, good water pressure in the shower. Would definitely stay again.
Guest favorite
Cabin in Cambridge
4.97 out of 5 average rating, 31 reviews

Pond View Cabin. Off-Grid, Rustic & Dog Friendly.

EmilyRating, 5 stars1 week ago
Highly recommend Brian’s off grid cabin! His directions were very helpful and made navigating the generator, camp shower, and other on-site details super easy to understand and execute. His property is beautiful and peaceful. We’re already looking at our calendars for another time to visit. Our dog, Stumpy, very much enjoyed the outdoor access and pond. He didn’t want to leave!
Guest favorite
Cabin in Brookline
4.94 out of 5 average rating, 17 reviews

Off-the-Grid Cabin in the Forest

AndrewRating, 5 stars2 weeks ago
Ideal cabin in the woods for a secluded forest getaway - well stocked kitchen, and the outhouse is 10/10. Very responsive and helpful!
Guest favorite
Cabin in Jamaica
4.93 out of 5 average rating, 60 reviews

The Woodland A-Frame

JannaRating, 5 stars1 week ago
This was a beautiful stay! My boyfriend, and his dog, really enjoyed our time here. I would highly recommend anyone to stay here! 10/10 would stay there again! ❤️
Top guest favorite
Barn in Town of Rockingham
5 out of 5 average rating, 12 reviews

Quiet Country Retreat

ArthurRating, 5 stars6 days ago
Ellie's apartment was gorgeous. The kitchen was beautiful and massive and contained everything you need. The bathroom was large and clean as well as the bedroom. I loved the deck which had a wonderful view of the mountains. It is a peaceful and lovely location. Ellie was very responsive and helpful. I had a relaxing time and felt truly refreshed after my stay.
Guest favorite
Tiny home in Ludlow
5 out of 5 average rating, 23 reviews

Alpine Reflection + Hot Tub

Madison QRating, 5 stars4 weeks ago
Pete’s cabin was absolutely stunning! 🤩 There was a breathtaking view of Okemo mountain with a 360 surrounding view of beautiful forest. Photos do not do the place justice. This was a perfect getaway for my boyfriend and I for the weekend. This tiny home feels spacious and roomy. We never felt cramped and had plenty of space for everything. Will definitely back back for another stay. Highly recommended!

Quick stats about vacation rentals in Windham

  • Total rentals

    60 properties

  • Nightly prices starting at

    R1,795 ZAR before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Frequently Asked Questions

  • 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.

  • Do house rentals in Windham have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Windham. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Windham?

    Experience the best of Windham with our house rentals, starting at about $150 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 wifi?

    Absolutely! We offer over 30 house rentals with wifi in Windham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Windham?

    Windham has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Windham?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 30 homes with a kitchen, over 30 homes with free parking, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Windham have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Windham. Enjoy a tailored experience with all the comforts you desire.

  • 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.

Destinations to explore

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  3. Vermont
  4. Windham County
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