
Vacation rentals with a patio in Windham
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Apartment rentals with a patio

Steps away from lift- Okemo 1B
Excellent location for skiing. I do not think I have ever stayed this close to the lift. Being able to stop by the apartment for lunch, or simply to warm up is a huge perk. It can be a bit loud from the lift and the groomers but it wasn’t an issue for us. The apartment is very comfortable for 2 adults and 2 kids.

Modern river apartment near lake, hiking, golf #3
Wonderful place to stay, thank you for having us 😁

Green Mtns of Vermont Hike/Fish/Swim/Shop/Explore
My friend and I booked a stay here on Memorial Day weekend when it became clear our camping trip would be rained out. We had such a wonderful time at Dana’s place! The space was immaculate and the bedrooms were very comfortable. The skylights throughout provide natural light, which contributes to the calm atmosphere. Even though we weren’t able to camp, we were still able to make s’mores on the fire pit and got some great hiking in nearby. Dana was a wonderful attentive host, and provided great recommendations for things to do in the area. We would definitely return!

Historic Victorian - Entire 3rd floor
Our stay couldn’t have been better. The listing matched reality perfectly—stairs and all—and the hosts stayed a step ahead with friendly, detailed messages and a useful house guide. The location is superb: an easy stroll to everything in North Adams and a great jumping-off point for exploring the Berkshires. The home itself was spotless, cozy, and wonderfully quiet. The hosts were extremely understanding of a minor issue (our fault) that occurred. We thoroughly enjoyed our visit and would gladly return.

The Inn at McCooey Drive, Manchester Vermont
Stayed there for weekend at Battenkill fly fishing festival. Accommodations were perfect. Everything is described. Private, quiet, beautiful views, immaculate inside, comfortable beds, clean, quiet, plenty of space and charming Norman Rockwell Vermont ski type Homestead. Highly recommend.

Minimal organic hideaway inspired by nature
Katherine’s space was so cozy! It was exactly what I needed for a retreat from daily life. I found both the loft and the daybed very comfortable. There were dimmers on most of the light fixtures, which was important to me because I like low-light settings. The kitchen included a counter with stools and was really quite beautiful. This Airbnb was within walking distance to a local restaurant, the general store and a food co-op. I decided not to rent a car because I was there for R&R., however , if you had a car, just a few minutes outside of town you would see beautiful trees all with leaves in there spring splendor. You could get to Brattleboro in about 20 minutes if you’re looking for more choices of restaurants.. (I decided to take the train up so I took a taxi to the Airbnb from the train and back to the train at the end of my trip.). Although it rained most of the time I was there, it was perfect for my goal of R&R.

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT
Really clean and perfect for what we needed it for! We were there to move out our daughter from Williams College and it worked out perfectly.

New Resort Condo Close to Lifts
We had a great stay here. It has everything you need in a decent sized charming space. Would highly recommend.
House rentals with a patio

River House w/ Hot Tub! Close to Mountain & More
This house was the best ski weekend away! Conveniently located yet secluded for a peaceful stay. The home itself is spacious, charmingly rustic, and thoughtfully stocked with everything we needed—especially the fully equipped kitchen, which made cooking a breeze. The atmosphere was cozy and inviting, making it the ideal spot to relax and unwind. Highly recommend.

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets
Ab’s home is absolutely beautiful and charming. My family and I stayed there for a long weekend and had no trouble finding it or getting in. The kitchen and bathrooms are all updated, and the whole place feels homey and peaceful. We used the grill one evening and realized the propane tank was empty, so I messaged Ab and he pointed us to a hardware store we could bring it to have it exchanged for a new one. He apologized for the inconvenience and reimbursed us for the cost of exchanging the tank, plus a generous bonus for our troubles. This was not Ab’s fault by any means – he said he had just replaced the tank two guests before us so it shouldn’t have been empty, but we didn’t mind the quick trip to have it replaced and truly appreciated his thoughtfulness and communication throughout the process. I’d recommend Ab’s place to anyone looking to stay in the Windsor area!

Minutes from Stratton Mountain
Theresa's place is a hidden gem off of Vermont's scenic route 100. My husband and I with another couple of friends stayed there for a weekend as we came to explore the green mountain forest area. The property is conveniently located at 5-10 min driving distance from local restaurants and cafes. There is also a grocery store and gas station nearby. The house itself has a cozy, rustic charm and is stocked with various books, board games, DVD classics, etc for entertainment. The kitchen has all the cutlery, pots and pans, required to cook a meal or two. The bedrooms are cozy each with a window opening onto lush green forested surroundings. Theresa was very responsive and accommodated our request for a slightly early check-in as one of us was travelling with a hip issue. Overall, I would highly recommend staying at Theresa's idyllic home.

Mountain View Getaway
We loved our stay at Nicole’s place. It was very peaceful and private- just what we needed! Our dog also felt right at home thanks to her welcoming touches. We would definitely stay there again!

Vermont Mirror House
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!

Black Star Barn, Mountain Retreat w/ Hot Tub
We were 2 couples and had the perfect stay! Really cozy house with a great porch and hot tub! We loved playing ping pong as well! Would 100% stay there again!!

Spectacular Farmhouse on 11 Acres (Dog-friendly)!
We had a great time at the Farmhouse! The house was very spacious and very well equipped to meet all our needs. We loved the property, very private on 11 acres, which our dogs loved as well!! Melanie was a great host, very responsive and friendly. We enjoyed a hike with our pups on Butternut Hill trail which was nearby. The Farmhouse is centrally located to the towns we like to visit. We had a great dinner at SoLo Farm & Table, I highly recommend the restaurant. Hope to return soon! Mike & Colleen
Condo rentals with a patio

Main St Escape | Explore Downtown Ludlow
Clean, great location, easy check in/out, and friendly host - would definitely stay again.

Dog-Friendly Mtn Escape/AC/Pool/
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

Slopes N Seasons | Trailside Condo at Mount Snow
This place is so welcoming and tasteful. Lots of in-house activities for the evening, when it's raining, or just when you feel like staying in. An easy recommendation.

Seasons Lodge | Trailside Condo w/ Fireplace!
Perfect place for a family stay at Mount Snow. Convenient ski on/ski off location just as advertised. Clean and comfortable. The sports complex is great spot for after skiing with full fitness center, pool, hot tub and locker rooms. Would definitely rent again.

Perfect 3 Br. Getaway Condo in Stratton, Vermont!
Lina was so responsive and helpful. Location could not have been more perfect. Such a lovely find! Thank you, Lina!

Condo w/ great amenities 4-seasons! Ski in Ski out
Excellent location and central to all things fun in southern Vermont. Loved the sports center amenities. Very peaceful considering it was end of mud season and not busy at all. We used the pool, workout facilities and locker room. Even had a fireplace we could use ! Christine was incredibly responsive and welcoming. Would recommend to others and would stay again if in the area.

CozyCub - Pool, Hiking, Mountain Biking
⭐️⭐️⭐️⭐️⭐️ Perfect Father–Son Getaway at CozyCub! My son and I stayed one night at the CozyCub condo in Killington, and once again, Dan and Holly delivered a flawless experience. From the moment we arrived, everything was spotless, cozy, and thoughtfully arranged—exactly what we look for in a mountain bike trip base. Comfort & Cleanliness: The condo was pristine, with comfy beds and fresh linens—like a home away from home. Attention to Detail: Every essential was readily available, from kitchen basics to crisp towels. Perfect for a Duo: Ideal layout and amenities for just the two of us—no waste, just well-tailored space. Consistent Excellence: We’ve stayed with Dan and Holly before, and CozyCub continues to meet our high expectations. This stay earned a full five stars. Thanks again to Dan and Holly for providing the perfect retreat—we’ll be back for our next biking adventure together!

Ski Condo 5 Min from Mt Snow
Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!
Quick stats about vacation rentals with a patio in Windham
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ514 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Pats Peak Ski Area
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Ragged Mountain Resort
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Clarksburg State Park
- Brattleboro Ski Hill
- Bretwood Golf Course
- Hooper Golf Course
- Ekwanok Country Club