
Holiday rentals with outdoor seating in Charlemont
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Top-rated rentals with outdoor seating in Charlemont
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Popular amenities for outdoor seating rentals in Charlemont
House rentals with outdoor seating

Secluded Farmhouse Retreat - stunning views
Mark's High Pocket Bed and Barn was absolutely stunning and cozy. My friends and I stayed while attending a wedding nearby, and were so delighted by the home the minute we walked in. Thoughtful furniture and decoration through out the house, as well as beautiful yard and walking paths that were so nice to explore on a sunny spring day. The home was immaculately clean and well stocked. Mark was very communicative and responsive. We would all very happily stay at this home again!

Cozy Modern Sugar House with spectacular views.
We had a delightful few days at this lovely home. It is comfortable, has fantastic views and was well stocked. We mostly just chilled, enjoying coffee on the deck, reading, watching the moon rise over the mountains and good conversation. Vermont is special and so is the sugar house, we would definitely return. I can imagine how beautiful and cozy it would be in winter time, watching the snow fall.

Green River Cottage-A Peaceful Country Retreat
we will definitely be back here in warmer/fall weather. it was so peaceful and the kids loved it, so did my husband and I. the home was beautiful and I loved the fully stocked spices and bathroom of things you may not think to bring with you on vacation.

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

Vermont Sugar House Retreat
This home is certainly one that feels like home when you walk in the door! The warmth of the wood and decor, and little touches throughout, let us know how loved this home is. We had everything we needed for our 2-plus week stay, and our hosts were incredibly responsive and kind. It was lovely to hear the owls and running water at night, and I can imagine how lovely the fireplace would be to use during the colder months! Thank you for a lovely stay!!!

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!

19th c. Barn in The Berkshires
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

Sunrise on the Water's Edge - Riverside Bungalow
What a great spot! Beautiful views on the river and a good spot for a family of 5 to use as home base while visiting Six Flags. Top notch host, thanks for everything Zuhair!
Apartment rentals with outdoor seating

Shakespeare’s Folly Side Farm and AirBnB.
William is an excellent host and his place is wonderful. I’ve stayed with him. Multiple times. Recommended!

Quiet St in Town, gardens, terrace
I made the right decision when I chose to stay at Jaki's place. The kitchen was fully equipped so that I could prepare my meals at home and the private deck was a bonus. The location was quiet and felt tucked away, while only being a five-minute walk to downtown. The check-in process was super easy and Jaki made it her priority to ensure I had everything I needed for a pleasant stay.

Overlooking the city in a quiet 7 unit building.
We enjoyed our stay at Tom's place. It was spacious, well appointed and clean. The birds and squirrels in the nearby trees were entertaining. The location was excellent for exploring North Adams on foot and nearby towns/parks. Tom was helpful and responded quickly to all our questions. I would highly recommend staying here.

Apartment with a view
Excellent place, great hosts. Easy. Just what we wanted.

Experience Three Sisters Sanctuary
Amazing stay at Richards. It is like the photographs and so much more. Richard was friendly and helpful and enjoyed sharing his home, sculptures and gardens with others. The apartment is beautiful and peaceful and a great getaway. He has put so much love and energy into his home and property and we are so lucky to be able to enjoy it also. I look forward to returning. A nice escape into the country side of western mass but still close to so many adorable small towns, farms, Northampton and fun little back roads.!!!

Sunny Peaceful Home
I highly recommend this airbnb. It was spacious, lovely, and well stocked. Jenny has thought of everything anyone could possibly need while away from home. I don't think I've ever stayed anywhere so well appointed. In addition, the space was beautifully set up, peaceful and quiet. Thank you so much for a lovely stay!

The Beer Diviner Brewery Apartment
Cute room above the brewery was a nice get away for my wife, our little dog, and I. John was friendly and so were all of the other employees and guests. The Irish band was great and the patio by the brewery was very cozy the beers were also delicious too. The room itself was spacious and well furnished with a good size bed and additional day bed. Fun weekend get away for all ages.

Globetrotter Retreat - Minutes to the Mountain
We had a great 4 day stay at Nina’s place. The apt is exactly as pictured and described on Airbnb. The space was a nice size, the furniture comfortable with the bed on the softer side, really good Water pressure in the shower, good amount of kitchen ware To create breakfast and lunches and light dinners. We loved the proximity to town and yet how quiet the place was, and there is a river directly in back. Nina was very prompt in responding to questions and gave us great recommendations for hikes in the area. There is a great bookstore and a number of really wonderful gift stores with Vermont artist’s works a block from the apt. And about a mile down the road starfire bakery with truly amazing baked goods. Make it a priority to Go there and try lots of things! We really loved our stay at Nina’s place and hope we can return in the fall or winter.
Apartment 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
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.

Summer 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 was a great host. The condo was as described. The place was clean and well organized, very cute and cozy. Christine was very responsive and helpful. I will definitely stay here again.

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!!

Mountain View Ski Escape
What a fantastic family weekend (2 families, 5 kids total ages 10 to 6). Andrew was super responsive to questions we had about the sleep set up (two bunks as well as a large single bed w/ trundle) for the kids. But more importantly, he was proactive! He sent clear notes on check in, how to get a fire going, local amenities, shuttles and more. The Community Center was fabulous; a large indoor, heated pool and hot tub, game room, library, TV room w/ bean bag chairs, common room w/ fire, popcorn, hot cocoa and even a little apres ski party on Saturday from 4-6pm. The condo is super close to Mt Snow, easy to find and park. Andrew even had sleds in the front closet which came in handy when the lifts shut down due to wind (but sledding in the backyard was a breeze). Highly recommend this great tri-story condo!

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!

Lovely 1bedrom apartment with screened in porch
Beautiful and very clean space! We had the most wonderful long weekend at Goran's apartment. He was so responsive and super friendly... cannot recommend enough. We will be back!
Quick stats about holiday rentals with outdoor seating in Charlemont
Total rentals
10 properties
Nightly prices starting at
₹8,677 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
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- Stratton Mountain
- Six Flags New England
- Monadnock State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
- Norman Rockwell Museum
- The Shattuck Golf Club
- Beartown State Forest
- Bright Nights at Forest Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Hildene, The Lincoln Family Home
- Brignole Vineyards