Vacation rentals with outdoor seating in Stockbridge

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Popular amenities for Stockbridge outdoor seating rentals

House rentals with outdoor seating

Guest favorite

Home in Granville

5 out of 5 average rating, 19 reviews

Stay by the Mettawee

IdaRating, 5 stars3 weeks ago
This place screams Airbnb! Spacious enough to entertain without being crowded, yet cut up for privacy as well. The hosts were very responsive and friendly!
Superhost

Home in Killington

4.75 out of 5 average rating, 4 reviews

| Launch Pad at Powder Day Chalet |

AmyRating, 5 stars1 month ago
Ashley's place is great! It only took us about 5 minutes to get to Killington, which was sweet. There's also a load of restaurants about 3-5 minutes away so lots of options. The house was as described and felt very cozy and comfortable.
Guest favorite

Home in South Woodstock

4.88 out of 5 average rating, 25 reviews

Grange Hall, South Woodstock Historic Home

EvanRating, 5 stars3 months ago
Great spot in a wonderful area. You really can't beat the location. The spot is very clean and well appointed. We were quite busy and didn't get to enjoy the deck out back, but the grill, solo stove and hammock were all great touches. The beds were all comfortable. One of the bathrooms was out of commission due to a leak, and Emily was in contact with us before we we arrived with a suitable alternative. While the listing doesn't specify that you have access to the entire home, we all assumed that we did. Nobody else stays in the home while guests are there, but the usable space felt small for what was paid. It was still a wonderful spot and a great stay and I would easily recommend it.
Guest favorite

Home in Barre

4.85 out of 5 average rating, 456 reviews

City Heights

EstebanRating, 5 stars5 days ago
great place to stay, plenty of room for everyone. very well equiped and the decoration is a plus! James really put an effort on making everything beautiful for guests. highly recommended and would book again if coming back to Vermont
Guest favorite

Home in Plainfield

4.89 out of 5 average rating, 138 reviews

Historic Home on 17 acres of land. Go escape!

LydiaRating, 5 stars3 weeks ago
This historic house is gorgeous and homely at the same time. It fit our big party just perfectly and had a lot of rooms for everyone to gather. All the utilities worked perfectly and the place was easy to find. It’s our second time staying here and it never disappoints. Definitely recommend staying here and will be back again!
Guest favorite

Home in Jamaica

4.92 out of 5 average rating, 49 reviews

Luxury Contemporary Home - Minutes to Stratton

ChristinaRating, 5 stars3 weeks ago
This property was absolutely stunning—spacious, modern, and impeccably clean with gorgeous views. The bedrooms were large and comfortable, and the bathrooms were spotless and stylish. We made great use of the sauna and pool table, which added so much fun to our stay. There were plenty of activities, and the space was perfect for relaxation and enjoyment. The host, Cherie, is really friendly and helpful in responding to any questions. Highly recommend for a luxurious getaway!
Superhost

Home in Killington

5 out of 5 average rating, 3 reviews

*Shred!* Discounted pricing! <10min to Snow Shed!

AlessandraRating, 5 stars3 weeks ago
Alan’s place at Killington was wonderful. New construction, only 10 minutes from the mountain and other Killington locations. Super directions and very responsive host - even gave great local recommendations. Beautiful kitchen and great amenities including a hot tub, sauna and wood burning stove. Wonderful stay, would stay again!
Guest favorite

Home in Grantham

5 out of 5 average rating, 19 reviews

Eastman Luxury Retreat Dartmouth College /Sunapee

LauraRating, 5 stars1 week ago
We had a WONDERFUL stay! The house is in pristine condition, very clean and modern and spacious. It looks exactly like the pictures. Helder was very responsive to any questions we had. We couldn’t have asked for a better experience and would certainly love to come back again!

Apartment rentals with outdoor seating

Superhost

Apartment in Northfield

4.83 out of 5 average rating, 106 reviews

River's Bend NEW 1-bd Apt - 8 Mins to Montpelier

GailRating, 5 stars2 weeks ago
We had a very comfortable stay. The setting on the river was quite peaceful, and the home was comfortable. It was a quick drive to Norwich University to watch hockey and visit our daughter, also a quick drive into Montpelier. The kitchen is well stocked for cooking meals in, and we enjoyed setting the puzzle. We will definitely stay again when we come back for another visit.
Guest favorite

Apartment in Chester

4.93 out of 5 average rating, 137 reviews

Lovely 2 Bedroom Apartment w/deck & pond view

DanielRating, 5 stars1 week ago
Hugh and Nancy’s place was great for a weekend of skiing at Okemo. Less than 15 minutes to the mountain and to the town of Ludlow. Check in was easy.
Guest favorite

Apartment in Waitsfield

4.89 out of 5 average rating, 163 reviews

Mad River Valley Ski Cabin

MollyRating, 5 stars4 weeks ago
great stay for family over holiday - thank you!
Guest favorite

Apartment in New Haven

5 out of 5 average rating, 220 reviews

Dog Team Falls Apartment - Minutes from Middlebury

AmyRating, 5 stars1 week ago
Great place to stay while visiting our daughter at Middlebury College
Guest favorite

Apartment in Middlebury

4.98 out of 5 average rating, 123 reviews

Mountain View Retreat

IelizavetaRating, 5 stars3 weeks ago
Beautiful view. Everything was spotless and very accurate to the listing. I would recommend to anyone visiting that area.
Guest favorite

Apartment in Middlebury

4.82 out of 5 average rating, 164 reviews

Cozy Apt. Near heart of Middlebury Fiber WIFI

KevinRating, 5 stars4 days ago
Directions were easy to follow and close to middlebury college for those visiting
Guest favorite

Apartment in Bristol

4.88 out of 5 average rating, 314 reviews

"Dragonfly Apartment" Private Bristol Apartment

JoleneRating, 5 stars1 week ago
What an adorable, peaceful Vermont neighborhood! We loved walking the pups around, being walkable downtown and the historic homes. The Dragonfly was cozy, warm and perfect for our ski weekend. Only 35 minutes to Sugarbush. We will definitely stay here again.
Guest favorite

Apartment in Hancock

4.99 out of 5 average rating, 114 reviews

Two-Bedroom apartment in the Green Mountains

PeterRating, 5 stars2 weeks ago
Booked a month stay at dick’s place. Central to skiing for our family. Cozy and functional space, we were comfortable and at home. Dick and Dorothy were lovely hosts. Hope to be back.

Condo rentals with outdoor seating

Guest favorite

Condo in Ludlow

4.98 out of 5 average rating, 115 reviews

Main St Escape | Explore Downtown Ludlow

AlexanderRating, 5 stars1 week ago
We had an amazing stay at Tommy’s place near Okemo Mountain! The house was spotless and very well-maintained, making it a comfortable and welcoming retreat. The location couldn’t have been better—everything in town was within walking distance, which was so convenient. The proximity to the mountain shuttle was a huge plus; it was right by the Airbnb, making it super easy to get to the slopes without having to drive. Overall, the experience exceeded our expectations, and we would absolutely stay here again. Highly recommend to anyone looking for a convenient and cozy spot near Okemo!
Guest favorite

Condo in Killington

4.94 out of 5 average rating, 161 reviews

Renovated unit, prime location! Shuttle on/Ski off

KimberlyRating, 5 stars3 weeks ago
All round great experience! Exactly as advertised-wonderful stay in Killington! Thank you for the wonderful and cozy accommodations!
Guest favorite

Condo in Grantham

4.96 out of 5 average rating, 113 reviews

Cozy Light-filled Condo in Charming Eastman

WilliamRating, 5 stars3 weeks ago
Perfect spot for our family holiday get together. Very quiet and relaxing visit. Lyn was a terrific host and went above and beyond to be sure we had no problems with our stay.
Guest favorite

Condo in Warren

4.97 out of 5 average rating, 122 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

RobertRating, 5 stars1 week ago
Cathy’s place was very nice. Clean and great location. Would definitely stay again. Our stay was short so we did not use the center facilities but looked nice.
Guest favorite

Condo in Killington

4.91 out of 5 average rating, 117 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

TerrenceRating, 5 stars6 days ago
Clean and convenient to the mountain, we would stay again. Great place.
Guest favorite

Condo in Killington

4.95 out of 5 average rating, 210 reviews

Walk/2min Shuttle to Lifts 2BR @ Mt. Green Resort!

TroyRating, 5 stars1 week ago
Condo was perfect location to ski lifts. Plenty of room for 4, comfortable furniture.
Superhost

Condo in Ludlow

4.83 out of 5 average rating, 118 reviews

Okemo Clock Tower Base Ski-in/Ski-out Condo

AlexanderRating, 5 stars1 week ago
Nice unit located very close to the Okemo lifts. It was fully equipped for cooking my own meals, which was important for my diet. I enjoyed skiing at Okemo and will come back again.
Guest favorite

Condo in Killington

4.82 out of 5 average rating, 255 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

JacquelynRating, 5 stars1 week ago
Perfect accommodation for our party of 5 adults (husband & I, adult children and a girlfriend). We would definitely stay here again. The condo is spacious and we never felt crowded. The kitchen is well stocked. An added bonus is the refrigerator has an ice maker and cold water, something you don't normally see at a rental. Beds were very comfortable and the linens were so soft. There were plush towels. We really loved the location...ski on ski off for Pico. The ski on is a narrow trail and was challenging for the recently categorized intermediate skier of our group. She opted for taking the shuttle back while the rest of us stayed out. We were slightly concerned about the ski off as B Slope was closed for race training. Thankfully by the time we were ready to end our day it was open. The ski off is really for a solid intermediate skiers. The hosts were great to communicate with and accommodated our request for an early check in.

Quick stats about vacation rentals with outdoor seating in Stockbridge

  • Total rentals

    50 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    3K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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