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Vacation Homes in Stockbridge

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (165)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2.0 star property
10.0 out of 10, Exceptional, (23)
"Pleasant hosts. My daughter milked s goat! Great night’s sleep."
The price is SAR 563
SAR 723 total
includes taxes & fees
15 Sep - 16 Sep
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (115)
"My husband and I came from Michigan and met family from Massachusetts to run the Covered Bridges Half Marathon! This spot was so perfect—we loved the coffee bar and just enjoyed how comfortable and homey the whole place feels. We would stay here again in a heartbeat!"
Beautifully renovated with fireplace and coffee bar

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (6)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

10.0 out of 10, Exceptional, (110)
"Nice rental for our family and the owner was very rsponsive."
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (25)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Country townhome - mountain view - walk to Village of Quechee - near Club & golf

9.0 out of 10, Wonderful, (36)
"Great location, cute condo, comfortable beds, modern kitchen."
Country townhome - mountain view - walk to Village of Quechee - near Club & golf

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (218)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (17)
"It was a wonderful stay in a beautiful home close to all of the places we wanted to spend time!"
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

New Listing - Luxury log home with stunning views

10.0 out of 10, Exceptional, (31)
"Beautiful house on an amazing piece of property. The house was very comfortable for two families of four. It has everything you could need and more. The hosts were very responsive. We will definitely stay here again."
New Listing - Luxury log home with stunning views

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (38)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (76)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Quechee - Four Season Resort Townhome

10.0 out of 10, Exceptional, (10)
"Very nice ski chalet with great kitchen, large and private bedrooms and a hot tub. Very suitable for a small family retreat."
Quechee - Four Season Resort Townhome

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

10.0 out of 10, Exceptional, (84)
"Alex's house is a great place to stay for a weekend getaway! The peace and quiet coupled with surreal mountain views made for a memorable trip with friends. "
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (72)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

10.0 out of 10, Exceptional, (64)
"The perfect place for our friends and family to stay!"
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.6 out of 10, Excellent, (27)
"The host and house manager are absolutely the best. Felt very taken care of - they went above and beyond."
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

10.0 out of 10, Exceptional, (48)
"Our family had a great stay in Ludlow for a four day ski vacation. Tom and Patti were great hosts and their home is convenient to both Okemo and Killington. The hosts communicated well with us and their place was perfect for our needs (family of 4), clean, and convenient to downtown Ludlow and restaurants. "
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Stockbridge Hotel Reviews