Vacation rentals in Stockbridge

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Top-rated vacation rentals in Stockbridge

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Guest favorite

Cabin in Royalton

4.99 out of 5 average rating, 174 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Apr 29 – May 6

$135 per night

Guest favorite

Guest suite in Royalton

4.96 out of 5 average rating, 179 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need and even a few extras like farm fresh eggs in the fridge and hot chocolate. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

Jun 23 – 30

$102 per night

Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 205 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Jan 9 – 16

$137 per night

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 113 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Sep 14 – 21

$137 per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 128 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

Aug 6 – 13

$86 per night

Superhost

Home in Stockbridge

4.87 out of 5 average rating, 134 reviews

Escape to Vermont

Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.

Jun 23 – 30

$314 per night

Guest favorite

Apartment in Stockbridge

4.87 out of 5 average rating, 158 reviews

Rustic 64 Acre Woodland Haven on a Beautiful River

Peaceful 64 acre secluded retreat located in a forested valley, surrounded by a beautiful river, accessed by a private bridge, with private swimming holes and river beaches. Private full level apartment in a two floor house, with forest views from every window. Perfect for river swimming in Summer, leaf-peeping in the Fall, and winter skiing. Connected to VAST and VASA trails system. Appalachian Trail access. Two miles to the Wild Fern, 7 miles to I-89. 20 minutes from Killington.

Oct 10 – 17

$158 per night

Guest favorite

Cabin in Randolph

4.95 out of 5 average rating, 189 reviews

Secluded Log Home on 109 Acre Natural Wonderland!

Enjoy our remote, easily accessible, immaculate new log house, set in nature on 109 acres. Pond, woods, fields and trails; with high speed internet and smart TV! Sleeps 6, including a queen bed, 2 bunk beds, and a sleep sofa. Fully equipped kitchen, including a full-sized refrigerator, microwave, Keurig coffee maker and many other amenities. Screened in porch. Views from every room! In the heart of the ski corridor. Explore the trails, and the meditation yurt when available!

May 6 – 13

$112 per night

Guest favorite

Guest suite in Bethel

4.97 out of 5 average rating, 137 reviews

Two bedroom. Separate enterence.

Please be advised that during winter months you may need to walk up Winterberry lane and our driveway if you do not have an AWD vehicle with good snow tires. Two bedroom apartment in the heart of Vermont. Snowmobile trail located off lane. Snowshoe, hike, or mountain bike from the door. Quiet private location with separate entrance and parking onsite. Ramp to access apartment, with stair free access. Pond, views and located in the center of the state, a great place to start!

Jul 13 – 20

$110 per night

Guest favorite

Home in Bethel

4.84 out of 5 average rating, 127 reviews

Hike, run, swim or cycle in beautiful Central VT

Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

Dec 1 – 8

$114 per night

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 389 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Nov 27 – Dec 4

$122 per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 316 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins.

Nov 13 – 20

$118 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Stockbridge vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Stockbridge's top sights

Tozier's Restaurant17 locals recommend

Clear River Tavern23 locals recommend

Clear River Inn9 locals recommend

Swiss Farm Inn10 locals recommend

Green Mountain Trails16 locals recommend

Riverside Farm3 locals recommend

Other great vacation rentals in Stockbridge

Guest favorite

Tiny home in Pittsford

4.96 out of 5 average rating, 155 reviews

Charming tiny house with great VT location!

Jun 2 – 9

$104 per night

Guest favorite

Condo in Killington

4.88 out of 5 average rating, 199 reviews

Killington-Pico ski in/out Studio at base of Pico

May 12 – 19

$86 per night

Superhost

Chalet in Stockbridge

4.93 out of 5 average rating, 168 reviews

Killington spring ski - MTbike -new jacuzzi

Apr 26 – May 3

$249 per night

Guest favorite

Apartment in Chittenden

5.0 out of 5 average rating, 222 reviews

Vermont Country Suite

Mar 20 – 27

$113 per night

Guest favorite

Cabin in Leicester

4.98 out of 5 average rating, 711 reviews

Log Cabin Getaway near Middlebury and Green Mtns

Mar 1 – 8

$110 per night

Guest favorite

Condo in Killington

4.81 out of 5 average rating, 140 reviews

1BR Modern Condo @ Whiffletree Ground Fl Walkout

Jun 3 – 10

$84 per night

Guest favorite

Home in Pittsfield

4.91 out of 5 average rating, 149 reviews

Beautiful Mountain Log Cabin with Scenic Views

Sep 7 – 14

$420 per night

Guest favorite

Home in Killington

4.91 out of 5 average rating, 161 reviews

Cozy Condo Tucked in the Heart of Killington

Jun 2 – 9

$117 per night

Show all

Quick stats about vacation rentals in Stockbridge

Total rentals
120 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
4.2K reviews
Nightly prices starting at
$30 before taxes and fees

Frequently Asked Questions

Are there family-friendly vacation rentals in Stockbridge?
Stockbridge has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Stockbridge have wifi?
Absolutely! We offer over 50 house rentals with wifi in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Stockbridge?
Four-legged friends are welcome in Stockbridge. Choose from more than 50 vacation rentals for guests traveling with pets.
How much does it cost to stay in chalet rentals in Stockbridge?
Experience the best of Stockbridge with our chalet rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Stockbridge?
Yes! Work meets play with ease at over 50 vacation rentals in Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Stockbridge have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Stockbridge have free parking?
Absolutely! We offer over 10 bed and breakfast rentals with free parking in Stockbridge. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Stockbridge have a kitchen?
Absolutely! We offer over 10 cabin rentals with a kitchen in Stockbridge. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Stockbridge

Top-rated vacation rentals in Stockbridge

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Stockbridge vacation rentals

Stay near Stockbridge's top sights

Other great vacation rentals in Stockbridge

Tiny home in Pittsford

Condo in Killington

Chalet in Stockbridge

Apartment in Chittenden

Cabin in Leicester

Condo in Killington

Home in Pittsfield

Home in Killington

Quick stats about vacation rentals in Stockbridge

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there family-friendly vacation rentals in Stockbridge?

Do house rentals in Stockbridge have wifi?

Are there pet-friendly vacation rentals in Stockbridge?

How much does it cost to stay in chalet rentals in Stockbridge?

Are there vacation rentals with a dedicated workspace in Stockbridge?

Do house rentals in Stockbridge have air conditioning?

Do bed and breakfast rentals in Stockbridge have free parking?

Do cabin rentals in Stockbridge have a kitchen?

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