Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Our top choices for Stockbridge holiday homes

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

☆ 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

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, (21)
"Pleasant hosts. My daughter milked s goat! Great night’s sleep."
The price is AU$357
includes taxes & fees
6 Sept - 7 Sept
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Converted Carriage Barn | The Carriage House Unit1

9.8 out of 10, Exceptional, (21)
"Charming, comfortable, beautiful place. Felt like home and was everything you could want from a converted barn in Vermont!"
Converted Carriage Barn | The Carriage House Unit1

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

2.0 star property
9.8 out of 10, Exceptional, (75)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

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

Custom-built Tiny House on forested lot near Quechee

9.8 out of 10, Exceptional, (60)
"Arturo and John are incredibly thoughtful and attentive hosts. They have considered every possible need and detail in the space. It’s beautiful, homey, and full of personality. The hot tub is a dream. We loved the location. It was easily to get to Woodstock, restaurants, and sightseeing, while still feeling remote and secluded. 10/10 would stay here again! "
Custom-built Tiny House on forested lot near Quechee

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (55)
"Cozy accommodations, great location, beautiful property, wonderful hosts."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Converted Carriage Barn | The Carriage House Unit2

9.6 out of 10, Exceptional, (4)
"Very cool conversion of an old barn. Very comfy and rather iconic. Because of the barn construction, there was an occasional encounter with a bug or two. Nicely located with many shops and restaurants nearby. The surrounding neighborhood of Quechee is very pleasant and kind of upscale country. Be aware there are no hangers/closets/ironing board/washer/dryer, so plan accordingly."
Converted Carriage Barn | The Carriage House Unit2

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

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

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

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

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

9.8 out of 10, Exceptional, (37)
"Great property, cozy and well maintained!"
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

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 & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (221)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

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 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!!!

BRIDGEWATER RETREAT

10.0 out of 10, Exceptional, (7)
"A true gem."
BRIDGEWATER RETREAT

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

9.8 out of 10, Exceptional, (215)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Pet-Friendly! Hot Tub | Marsh Family Road Retreat

9.2 out of 10, Wonderful, (9)
"The house was clean and the beds were comfy. Unfortunately due to the weather we didn't get to enjoy the deck but there was ample space inside to hang out. We had a question when we first arrived and the host was very quick to respond which is always much appreciated. "
Pet-Friendly! Hot Tub | Marsh Family Road Retreat
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

Find out more about Stockbridge

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
Accommodation
785 Holiday Homes
Lowest Price
AU$357
Highest Price
AU$357