
Vacation rentals with outdoor seating in Windham County
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Top-rated outdoor seating rentals in Windham County
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House rentals with outdoor seating

Spacious Brattleboro home on river, walk to town
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.

Frosted Willows
I had a wonderful stay while visiting Brattleboro for work. The house is just lovely and extremely comfortable. The kitchen had everything that we needed. I’m hoping to stay again in the future when working in the area.

Hot Tub & Game Room - Ski Mt. Snow/Stratton
We truly enjoyed staying here!! The hosts were amazing! They gave us plenty of local recommendations that made our stay so enjoyable. The home was wonderful. Plenty of this to do if you don’t want to leave. Game room was a great bonus!! We can’t wait to return!

Magic Creek
Cute Vermont farmhouse that had everything that you needed. We enjoyed Cooking inn and hanging out in the living with the fireplace. The hot tub was so much fun after a cold day on the mountains. There is a cute little coffee shop and super market only 10 minutes away.

Cozy Home for 2-5 People in Vermont
Clean and comfortable. Great host who goes above and beyond to make his guests feel comfortable and at home. The beds were comfortable and the bathrooms clean. This place has everything that I look for in an AirBnB stay. We hosted a get together for a dozen family members who live in the area. They were the reason for our trip. People gathered in small groups in the kitchen, living room, dining room and TV room. Plenty of room. It was like having company in my own home.

Wilmington A-Frame- Cozy and Convenient
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!

Cozy Riverfront Home in beautiful Jamaica
Great place. Very isolated and a beautiful location but still has all the creature comforts. The deck, view, and space are amazing. Fast WiFi, 2 bathrooms, and a dishwasher with garbage disposal are really cool in a rustic location like this. The wood fires hot tub was obviously the star of the show. Clear instructions and good communication for everything. The gas grill and gas fire pit were nice. Every thing was comfortable and great. Stress free. Hope to stay here again, thanks for everything.

Modern Spacious Home with Mountain Views
My family of four loved Christine’s place! She is so thoughtful, leaving yummy snacks plus necessities as well. She’s a great baker and provided us with some yummy treats! The beds were super comfy and cozy, bathrooms were clean and well-equipped and we loved being both close to downtown but also could go hiking out the back door. We feel so grateful to have had such a lovely and relaxing place to stay. Thank you, Christine! ❤️
Apartment rentals with outdoor seating

**Happy Hour! Gorgeous & Modern Downtown Retreat**
Beautiful apartment in the center of Wilmington. We own land and have our camper set up in the next town over, but with the cold weather lately, the camper is still winterized. We wanted to come up and get some yard work done and stay locally, and this apartment was the clear winner! Walking distance to our favorite coffee shop, lots of restaurants, my favorite bookstore (!!) and walking trails. Loved the deck- even though it was April and iffy weather, we were able to have takeout dinner outside one night! So grateful that Jennifer allows pets, as we have two dogs and it’s often hard to find pet friendly Airbnb accommodations that are in a good location and as clean as this place! Jennifer was so kind, accommodating and responsive. She went out of her way to make sure we had a great trip- she’s definitely one of the best hosts we’ve had! Thank you for making this week wonderful! We will be back.

Quiet St in Town, gardens, terrace
We loved our stay at Jaki’s place! Very easy check in, easy to find, no issues at all. Very comfortable place and walkable to downtown. Would definitely stay here again!

Quaint cozy vermont apartment
Mariann has a great space in a great location. Very accommodating and friendly, made you feel very welcome . Very responsive. Really nice area. Would highly recommend.

Apartment with a view
The quintessential Vermont Airbnb! Beautiful surroundings, lots of outdoor activities, and easy to get into town with great restaurants. The hosts are very helpful and provide everything needed for a relaxing stay.

Globetrotter Retreat too - Minutes to the Mountain
Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

River View apartment
This property is definitely within the top five Airbnb’s that I’ve ever stayed at! The apartment is absolutely beautiful with no detail missed. The kitchen was impeccable with light snacks provided and coffee/creamer, which is a huge plus for me. The bathroom was spotless with beautiful, plush towels and a lovely washer and dryer set. The living room was very comfortable with a reclining couch. The bed was very comfortable with plush linens. I can’t wait to stay again when I’m working in town.

Vermont Getaway Apartment
This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!

Victorian Inn Apartment
beds comfortable. heating works well. everything works well.
Condo rentals with outdoor seating

Mount Snow Ski Chalet
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.

Slopes N Seasons | Trailside Condo at Mount Snow
We loved our stay! Everything was immaculate. New. Even ready with some fun board games and a Bluetooth speaker. The location was excellent, and we had a great time! We definitely recommend and would stay again.

Renovated Condo - 5 min walk to Mount Snow
beautiful condo, well maitained and bathrooms new and remodeled. Great location to the ski lifts. He woks great, walls are solid because we couldn't hear the neighbors and all units were full this weekend. Nice fireplace and wifi worked great for the kids and all big flat screen tv's were excellent. Easy kitchen to cook in for the whole family. Best condo we've stayed at in Mt. Snow. Owners answered all our questions and recommendations

Winter Dream! The Handle Lodge at Snowtree Condos
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Condo w/ great amenities 4-seasons! Ski in Ski out
Christine is very easy to work with and very responsive. she answered us back right away before and during our stay. the place is great! very cozy and comfortable. I can't wait to go back to her place next time we're in town!

Great 2 bedroom condo at Stratton Mountain
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

A Village location, Steps to the Lifts & Village
We loved staying at this property. The location is excellent for access to the village and the lifts. It is also cute to look out over the ice skating pond. It was clean, had all the kitchen amenities you would need to make food, and had fun ski-oriented decorations. It is also close to the hot tub and lounge area within the main building. It had everything we needed to make out ski weekend comfortable and memorable. Can't wait to stay again!

Magic Mountain Trailside Condo Ski In / Ski Out
Great place. I’d definitely stay there again. No complaints about the unit or location. —Fun mountain We got lucky with a powder day! If the beginner slope had been open it would’ve been “Ski in -Ski out” but it wasn’t, so we had a hike to get back to the place. —A skier suggested that I duck under the rope, but I wasn’t familiar with the mountain so I wasn’t comfortable doing that. -It should be mentioned since his unit is @ the Top of the slope and you have to hike it with your gear. I was fine, but it might not be ok for everyone. I guess sometimes you have to break the rules!!🤷🏻♀️ I’d recommend Tony’s place!
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Saratoga Race Course
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Ekwanok Country Club
- Baker Hill Golf Club
- Bretwood Golf Course
- Hooper Golf Course
- Dorset Field Club
- Clarksburg State Park
- Peebles Island State Park
- Hildene, The Lincoln Family Home
- Pineridge Cross Country Ski Area
- Stump Sprouts Ski Touring Center
- Willard Mountain
- Northern Cross Vineyard
- Things to do Windham County
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