Choose from 64 vacation rentals located in Stockbridge, Vermont. Top filters in Stockbridge include Kitchen or Kitchenette, Parking, and Internet / Wifi. Prices range from $71 to $2,843 per night. Our most popular vacation rental types near Stockbridge are Hotel and RV.

Top vacation rentals in Stockbridge

Property grounds
4.9
Outstanding(112 Reviews)
Killington area home - 4-seasons & hot tub. Sleeps 12+
House
 in Pittsfield
15 guests · 5 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette

This inviting House in Stockbridge can fit your needs for many types of vacations, at $440 per night.

$$$$
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Property view
4.7
Outstanding(142 Reviews)
Mountain Valley Retreat
Bed and Breakfast
 in Killington
1 queen bed
Garden · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Stockbridge? This Bed and Breakfast offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Smoking allowed, and more.

$$$$
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Property building
4.4
Excellent(207 Reviews)
Clear River Inn and Tavern
Inn
 in Pittsfield
2 full beds
Pets allowed · Kitchen or Kitchenette · Air conditioner

Soak up the beauty of Stockbridge in our Inn, Clear River Inn and Tavern. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Exterior
5.0
Outstanding(101 Reviews)
"The Crooked House" with A/C and sauna on private wooded lot near Killington
House
 in Stockbridge
8 guests · 3 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Most favorited

The best choice in Stockbridge for House, for $387 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Vacation rentals with a kitchen in Stockbridge

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Outdoor dining
4.8
Outstanding(61 Reviews)
Killington Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi
House
 in Stockbridge (Pittsfield)
8 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

This House in Stockbridge, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Property grounds
4.5
Excellent(71 Reviews)
'The Mill Stream House' Lux Rustic Home on River w/JACUZZI & fireplace
House
 in Killington
10 guests · 4 bedrooms · 2 baths
Pool · Pets allowed · Kitchen or Kitchenette

Indulge in a peaceful retreat at 'The Mill Stream House' Lux Rustic Home on River w/JACUZZI & fireplace , our elegant House in Stockbridge. Enjoy amenities including Dishwasher, Fireplace and Internet / Wifi, and more.

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Property grounds
4.8
Outstanding(55 Reviews)
"Whispering Pines" Ski House in the heart of the Green Mountains
House
 in Stockbridge
12 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Stockbridge at "Whispering Pines" Ski House in the heart of the Green Mountains for $868 for your next trip.

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Property view
4.5
Excellent(2 Reviews)
Killington Area Escape with Deck, Views and Hot Tub!
House
 in Stockbridge
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our House in Stockbridge has everything you need for a rejuvenating stay. Treat yourself to Killington Area Escape with Deck, Views and Hot Tub!'s exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$
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Stockbridge

Stockbridge travel guide

Let us help you plan your perfect Stockbridge vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Stockbridge, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Stockbridge?

  • Kitchen or Kitchenette
  • Parking
  • Internet / Wifi

What are the must-visit tourist attractions in Stockbridge, VT?

Stockbridge, VT is a small town in the Green Mountains of Vermont, with plenty of tourist attractions to explore. Here are some must-visit tourist attractions in Stockbridge, VT:

  • Robert Frost Wayside Trail
  • The Stockbridge Theatre
  • The Stockbridge Library Museum and Archives
  • The Old Mill Museum

The Robert Frost Wayside Trail is a great way to explore the natural beauty of Stockbridge, while the Stockbridge Theatre offers a variety of musical and theatrical performances. The Stockbridge Library Museum and Archives is a great place to learn about the history of the town, and the Old Mill Museum is a great spot to learn about the town's past. No matter what you're looking for, Stockbridge, VT has something for everyone!

How can I get around in Stockbridge, VT?

You can get around Stockbridge, VT in the following ways:

  • By car
  • By bus
  • By bike

You can also walk or take a taxi to get around the town.

Where can I find affordable accommodation in Stockbridge, VT?

Stockbridge, VT offers a variety of affordable accommodation options for visitors. Here are a few of the best:

  • The Stockbridge Inn: Located in the heart of the village, this inn offers cozy rooms with a variety of amenities.
  • The Stockbridge Lodge: This lodge offers rustic charm with modern amenities, and is conveniently located near the town center.
  • The Stockbridge Motel: This motel offers budget-friendly rooms with basic amenities, and is just a short walk from the town center.
  • The Stockbridge Bed & Breakfast: This charming B&B offers cozy rooms with all the comforts of home, and is just a short drive from the town center.

What is the culture like in Stockbridge, VT?

Stockbridge, VT is a small rural town in the state of Vermont with a population of around 500 people. The culture in Stockbridge is one of tradition, pride, and community. Here are five bullet points that represent the culture of Stockbridge, VT:

  • A strong sense of community and togetherness.
  • A deep respect for nature and the outdoors.
  • A focus on traditional values and small-town living.
  • A commitment to the preservation of the local culture.
  • A celebration of the small-town lifestyle and culture.

Is Stockbridge, VT safe to travel to?

Stockbridge, VT is safe to travel to. Here are some reasons why:

  • Low crime rate
  • Friendly locals
  • Beautiful scenery

Visiting Stockbridge, VT is an enjoyable and safe experience.

What are the popular shopping destinations in Stockbridge, VT?

The popular shopping destinations in Stockbridge, VT are:

  • The Stockbridge Marketplace: a family-run general store since 1803, offering local products and gifts.
  • The Stockbridge Country Store: a small-town store with a variety of products, from groceries to gifts.
  • The Stockbridge General Store: a classic general store, offering local and regional products.

What are the best neighborhoods to visit in Stockbridge, VT?

The best neighborhoods to visit in Stockbridge, VT are:

  • The Green Mountains
  • The White River National Forest
  • The Mad River Valley

These areas offer stunning views of the countryside, plenty of outdoor activities, and a variety of cultural attractions.

Where is Stockbridge, VT?

Stockbridge, VT is a small town located in the east-central part of the state, in Windsor County. It is bordered by the towns of Pittsfield, Bridgewater, and Granville, and is home to just over 400 people. The town is known for its 19th century architecture and its rural landscape.

What are the most popular vacation rental amenities in Stockbridge, VT?

The most popular vacation rental amenities in Stockbridge, VT include:

  • Fully-equipped kitchens
  • Free Wi-Fi
  • On-site laundry facilities
  • Outdoor recreation areas
  • Pet-friendly accommodations

These amenities offer vacationers the opportunity to enjoy a comfortable and convenient stay in Stockbridge. Fully-equipped kitchens allow guests to prepare their own meals and snacks, while free Wi-Fi lets them stay connected to the outside world. On-site laundry facilities offer the convenience of doing laundry without having to leave the property. Outdoor recreation areas provide plenty of space for activities, such as hiking, biking, and swimming. Finally, pet-friendly accommodations make it easy for travelers to bring their furry friends along for the trip.

What are the top things to do in Stockbridge, VT?

Stockbridge, VT is a great place to explore and have fun. Here are some of the top things to do in Stockbridge:

  • Visit the Gifford Woods State Park
  • Hike the Appalachian Trail
  • Explore the Calvin Coolidge State Historic Site
  • Visit the Quechee Gorge

Whether you're looking for a peaceful hike, some historical sightseeing, or just some time in nature, Stockbridge is the perfect place to visit.

What do I need to know before visiting Stockbridge, VT?

Before visiting Stockbridge, VT, there are a few things you should know. First, the town is quite small, with a population of about 500 people. Second, the town is located in the heart of the Green Mountains, so it's a great place for outdoor activities like hiking and skiing. Lastly, here are a few other things to remember:

  • Stockbridge is located in Windsor County
  • The town has a number of shops and restaurants
  • The town has a rich history, dating back to the 1700s

What is the price range for rentals in Stockbridge?

Vacation rentals in Stockbridge have a price range between $71-$2,843. The average price for rentals in Stockbridge is $634 per night.

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