
Holiday rentals with outdoor seating in Whitingham
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Whitingham
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Whitingham outdoor seating rentals
Holiday House Rentals with Outdoor Seating

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.

Modern 3-bedroom A-frame in Londonderry w/ Pond
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

The Gate House--Experience Vermont!
Pictures don't do Peter & Monique's listing justice. The home, the grounds & the surroundings are gorgeous in a way that isn't just picturesque but is peaceful & rejuvenating. Our family of 4 were staying here to attend the Williams reunion so we didn't get as much time as we would have liked to take full advantage of all the hikes, walks etc that the property location offered & almost wish we'd had more time. The AirBnb is exceptionally stocked, we've stayed in AirBnbs in the country & abroad & rarely do hosts provide things (like linens, coffee supplies etc) in adequate amounts let alone in excess of what might be needed for the number of guests X days being spent there. Not only were the hosts extremely generous but the quality of everything was excellent. We have family in different parts of MA and we asked the hosts if it was OK for our family to visit us at the property during the day & they graciously allowed that. Peter was extremely responsive & thoughtful in communications.

June in Vermont! (Pet Friendly)
This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
What an amazing experience! Our kids loved every second of it. Our hosts were amazing, responsive, and inviting. The home was beautiful and the scenery was spectacular. I highly recommend staying here. It was a great life experience! Thank you!

Cheerful 1 bedroom cottage
Glenn was incredibly kind and responsive, and the cottage was exactly like the pictures. The space was perfect for a couple-day getaway before starting my MFA! Also, if you need good local recommendations, Glenn has you covered.

Stunning mid-century house on 2.5 private acres
We were in the area for a wedding and this was a perfect alternative to the hotel options. A beautiful house - we would definitely stay here again.
Apartment rentals with outdoor seating

Sunny, light filled loft in 1873 Colonial
Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.

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!

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.

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.

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

Suite 23 - Spacious Sunny 2-BR with Mountain view
We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

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.

River View apartment
Susan's place is exactly as advertised and more. Very comfortable and well-equipped space with nice extras - coffee, tea, snacks, firewood and a grill with grill spatula, etc. Quiet, country setting that is a great value compared to hotels in the area. Would recommend and stay again.
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
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!

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
Perfect location to mt snow.. right across the street. It's an older complex but had everything we needed for a few days of skiing.. would rent again
Destinations to explore
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Pocono Mountains Holiday rentals
- Montreal Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Family-friendly rentals Whitingham
- Rentals with a patio Whitingham
- Rentals with a fireplace Whitingham
- House rentals Whitingham
- Rentals with a washing machine and dryer Whitingham
- Rentals with a fire pit Whitingham
- Rentals with outdoor seating Windham County
- Rentals with outdoor seating Vermont
- Rentals with outdoor seating United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- The Shattuck Golf Club
- Beartown State Forest
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Canterbury Farm