
Vacation rentals with outdoor seating in Whitingham
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Top-rated accommodations with outdoor seating in Whitingham
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Whitingham outdoor seating rentals
House rentals with outdoor seating

The Berkshires Mountain Terrace LUX Home Sleeps 7
This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.

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.

Charming House by Saratoga Lake - Prime Location
Rebecca's bungalow was a great place for our family, including our dog to stay. It's rare to find such a welcoming space for pets. Ample blankets and pillows were greatly appreciated as many hosts don't include these items. The space was larger than anticipated which was also a nice bonus. If you're looking for hospitality and location at an affordable price, definitely consider this as your next option if you're headed to Saratoga Lake.

Yellow Door House
We’ve stayed at Kathy’s Yellow Door many times, or kids call it our vacation home. Kathy is a great host and she will always strive to make your stay enjoyable and stress free (unless you have a toddler like we do). Don’t hesitate to stay at Yellow Door.

2.5mi from the lake! Fire pit, arcade, yard games!
Great spot! Stayed at Eric's place for a weekend with a group of college students (8) looking to hit the reset button and had plenty of space. It was spotless and comfortable, and we had no trouble finding what we needed. The virtual guide is also super helpful!

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Beautiful house in upstate with a hot tub and barbecue that allowed us moments that we won’t forget. Chris was very responsive and maintained the communication throughout our stay. The house was spacious, clean, great amenities and extra care from the host. The location was also good, close to Hudson but private. We loved it and hope to be back soon!

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.

The Gatehouse at Raspberry Ridge
If your looking for a great quiet stay while visiting Hudson or other local places this home is it. Very clean, super dog friendly. Close to the highways and hidden enough to really be apart of nature.
Apartment rentals with outdoor seating

Light filled three bedroom apartment DT Florence!
I chose to stay at Donna's a second stay because I appreciate the quiet neighborhood and very, clean comfortable home. Communication with Donna is easy and friendly.

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!

"Up Top” at Ro & Oak House
Had a great time at Hannah’s place. Excellent location, beautiful space, comfortable beds. No complaints!

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!

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.

River View Apt in Shelburne Falls Historic Village
Thanks Crystal It was a great spot for the weekend and very comfortable!

Quiet bright & sunny 2 bedroom apartment w/ porch
It was a great experience, very easy to get to.Super clean we enjoyed our stay!!

Sunny Troy Private Deck Parking Wi-Fi Top Floor
This is a great place, and I experienced very helpful communication and a restful stay. Would consider this location and Susan’s others in the future!
Condo rentals with outdoor seating

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

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.

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!!

Lovely 1bedrom apartment with screened in porch
Goran's home was very comfortable and we enjoyed many things. The architectural features were top notch with many luxurious details, such as the decorative tiles, the vaulted ceiling, and the large deck. We enjoyed the natural light, and the spacious rooms. The mattress was very comfortable, and we hope to return for another stay. I highly recommend Goran's home. Tracey deJong

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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- Stratton Mountain
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Saratoga Spa State Park
- Albany Center Gallery
- Saratoga Race Course
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Norman Rockwell Museum
- Bousquet Mountain Ski Area
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Ekwanok Country Club
- Hooper Golf Course
- Bretwood Golf Course
- National Museum of Racing and Hall of Fame
- Huck Finn’s Playland, Albany
- Peebles Island State Park