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Compare 545 Vacation Homes in Stockbridge with updated reviews, rates, and availability.

Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (74)
"Nice decor, a lot of personal touches and thought put into making the stay here very nice. Id totally stay here again or refer others to stay here. Quiet and removed but very close to town, nature hikes, and quaint eateries and gift shops."
Beautifully renovated with fireplace and coffee bar
Spacious country home, beautiful sunsets, 40 acres
10.0 out of 10, Exceptional, (21)
"Hosts are excellent communicators, and property is accurately described. When I arrived, there was an alarm going off on the stovetop. I didn’t want to bother the host, but I did reach out the following morning, and within minutes, I received a response which immediately solved the problem (reset breaker). This provides an excellent location to visit life-long friends in the area, with the convenience of a great kitchen. (We are already quite familiar with the surrounding area.) The...
Spacious country home, beautiful sunsets, 40 acres
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
10.0 out of 10, Exceptional, (90)
"We had a great stay at this property, it had everything we needed for our family of 5 for several weeks of temporary living. Comfortable and quiet space and close enough to stores, etc. "
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
4 Season Secluded Lakefront Home near Ski Mountains
9.4 out of 10, Exceptional, (61)
"This is now on our top 10 vacation lists. It is an outstanding location. The water quality is great, and there's a perfect little beach for the very little people. The house is rustic but has everything one might need. The variety of boats allowed us to see around the lake. We hated to leave."
4 Season Secluded Lakefront Home near Ski Mountains
Slopeside Chalet - Ski to and from your home!
10.0 out of 10, Exceptional, (7)
"Views are incredible! Already thinking of rebooking! Thank you "
The price is ¥32,912
¥104,297 total
includes taxes & fees
Oct 10 - Oct 11
Slopeside Chalet - Ski to and from your home!
Blueberry Hill Escape Pet Friendly HotTub Fire pit
9.8 out of 10, Exceptional, (12)
"On arrival I loved the breathtaking views of the mountains ! The house was so spacious. Each kid had their own room and my husband and I loved having a master suite ! Our dog was so comfortable there as well ! I am really big on cleanliness and this house was immaculate !! We loved the hot tub! So relaxing ! I walked the dog around the house every morning and had noticed fruit trees ! The peaches were delicious ! Got Home from dinner one night amd we were getting of the car and a black bear...
The price is ¥31,681
¥84,725 total
includes taxes & fees
Sep 30 - Oct 1
Blueberry Hill Escape Pet Friendly HotTub Fire pit
Cozy private country setting - 15 miles from Woodstock
10.0 out of 10, Exceptional, (20)
"A lovely spot to stay! Great communication with the host!"
Cozy private country setting - 15 miles from Woodstock
Log manor on 65 private acres of land with entertaining amenities & hot tub
9.8 out of 10, Exceptional, (6)
"Great property and beautiful views. Not too far from Killington. A wonderful trip to remember. Would definitely stay here again."
Log manor on 65 private acres of land with entertaining amenities & hot tub
Historic Schoolhouse in Rural Vermont Beauty Spot
10.0 out of 10, Exceptional, (24)
"The schoolhouse was just what we were looking for- a quiet country location with good walking, hiking, exploring, and close to Randolph. We appreciated the ephemera- books, maps, newspapers. Looking through the shelves and cabinets was an adventure unto itself. We spend time outdoors so one plus would have been more comfortable outdoor furniture. Thank you, Terrie, we have a terrific time!"
Historic Schoolhouse in Rural Vermont Beauty Spot
Luxurious guest home with private art gallery in the heart of a historic village
10.0 out of 10, Exceptional, (9)
"Beautiful property! Walking distance to shops and restaurants in Brandon."
The price is ¥50,075
¥64,345 total
includes taxes & fees
Oct 8 - Oct 9
Luxurious guest home with private art gallery in the heart of a historic village
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (150)
"Beautiful lake, kayaking, backyard firepit, hiking , such a fun area with a lot to explore.nearby, "
Idyllic Lakefront House Suited Two Families
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (198)
"We had a great and restful stay. The house was exactly as listed. Views were great with ducks, beaver and a family of deer. Good fishing from the dock. This is in my top 3 of all places at which we have stayed! Definitely recommended!!!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
9.8 out of 10, Exceptional, (30)
"Had a nice summer kickoff weekend with a few friends and their families. House had all the necessities and was a great layout for group meals and fire pit action."
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Custom-built Tiny House on forested lot near Quechee
10.0 out of 10, Exceptional, (45)
"The tiny house had everything I needed. I was in the area visiting family so I was out a lot but if you plan to stay in there is enough here to keep you busy. Centrally located to the highways and fun activities. Arturo was a wonderful host .we were in contact (not for any problems or issues) and he always responded promptly . You will enjoy your stay here. to keep you busyto keep ywonderful"
Custom-built Tiny House on forested lot near Quechee
Spacious 3-story home near ski area with private hot tub, Ping-Pong
6.8 out of 10, (13)
"Enjoyed our stay. The home was cozy with lots of amenities. "
Spacious 3-story home near ski area with private hot tub, Ping-Pong
The Cottage On Main Street
9.8 out of 10, Exceptional, (17)
"The home was very clean."
The Cottage On Main Street
The Brandon Inn - Fourth Floor Queen Room
9.4 out of 10, Exceptional, (3)
"This is a great spot. Was in town w Gus my field spaniel and we had a nice time at the Inn. The room was a bit antiquated but that’s part of the charm. We hiked the green mountains/silver lake trail and this place was perfect to rest weary bones. The rates are very reasonable and the property is quite beautiful. Will be back! "
The price is ¥20,976
¥26,741 total
includes taxes & fees
Oct 20 - Oct 21
The Brandon Inn - Fourth Floor Queen Room
Country townhome - mountain view - walk to Village of Quechee - near Club & golf
9.4 out of 10, Exceptional, (28)
"The youngest of our party was 81. Spiral staircase with luggage proved challenging. Wi-fi password access would have been most helpful. Tried opening doorknob after entering code. Very unsuccessful. Too old and dumb to open lockbox for key. Otherwise, very wonderful tourist visit and very appreciative overseas Korean guests seeing magnificent Vermont for the first time. "
Country townhome - mountain view - walk to Village of Quechee - near Club & golf
Merry Maple Getaway
9.6 out of 10, Exceptional, (16)
"Great property for a ski trip!!! Location is perfect to hit multiple resorts. The house was clean and exactly what was expected per the listing."
Merry Maple Getaway
Lovely Brookfield Home w/Private Deck & Views
10.0 out of 10, Exceptional, (16)
"My family stayed at Winderlea for 2 nights to attend a family party. This house was absolutely perfect for us! There was so much space & privacy and many places to gather. The house was beautiful and fully equipped with everything we needed. I honestly can't say one negative thing. The property surrounding the home was gorgeous and peaceful. Brian greeted us at the property and was so nice. We give it ☆☆☆☆☆!! furnished and "
Lovely Brookfield Home w/Private Deck & Views
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Other property types in Stockbridge

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (463)
"If you’re looking for rest and relaxation this is it. You are one with nature at this cabin which has everything you need. Host was very nice and accommodating. Plenty of yard games for the family and trails to explore. Hope to be back in the future. "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (38)
"Absolutely perfect! Very nice location. Quiet and cozy little townhome. Short drive to Bear Mountain and Killington Ski Resort. Amazing area with plenty of awesome views."
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (209)
"Jeff is a very gracious host and kept in communication throughout this VRBO experience. The cabin is a wonderfully enchanting place with a lot of privacy, and everything you need to make your time spent there a very relaxing and rewarding experience. The cabin is within 20 minutes of Stowe, Vt. The culture is downhome and the food is great!!!!"
Cozy Loft for two with Hot Tub
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.