Vacation rentals in Stockbridge

4.98 out of 5 average rating, 146 reviews

A log home features a spacious deck overlooking the lake, with seating areas and a hammock. Large glass windows provide a view of the serene outdoor space, including a manicured lawn and easy access to a wooden dock.

Apartment in Fairlee

Kismet Cottage, Perfect for longer stays

Welcome to your home away from home! This charming, fully-furnished 1-bedroom apartment sits right on the lake, offering serene views and a peaceful retreat after a long shift. With four major hospitals located within a 30-minute commute, this is the ideal spot for traveling nurses looking for comfort and convenience. Everything you need is here from a cozy queen bed to a fully equipped kitchen and comfortable living space including a laundry room so you can stay fresh and ready for your shifts.

5 out of 5 average rating, 5 reviews

A serene outdoor space features two Adirondack chairs positioned around a fire pit, surrounded by lush green grass and a backdrop of dense trees. The calming natural setting invites relaxation and outdoor gatherings.

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

Recently renovated 2BR/2BA cottage in Mendon, VT, near Pico & Killington Ski Resorts, & Rutland. Sleeps 6: 1BR w/ queen & ensuite, 2nd BR w/ 2 double beds. Additional BA, laundry room, living room w/ smart TV, fully equipped kitchen & dining area. High-speed WiFi, mini splits for heat/AC, front & back decks, BBQ grill. All new furnishings offer modern comfort & rustic charm. Ideal for skiing, exploring, or relaxing in the mountains. Perfect base for your VT adventure! Discounted ski rentals.

4.89 out of 5 average rating, 9 reviews

A grassy area features a fire pit surrounded by several white Adirondack chairs. A large tree provides shade beside the inviting white house, which has multiple windows and a porch. Scenic views of the landscape are visible in the background.

Home in Poultney

Snowberry Farm Home Sweet Home

This memorable place is anything but ordinary. Hike the hayfields on the mowed paths! Fish in the Pond and enjoy the peace and quiet of this comfortable and spacious home. Star gazing is on the menu too! One mile to rail trail for bike enthusiasts. This house is very welcoming & well equipped for entertaining family & friends. Room for everyone & extra space for quiet reading & conversation. Cider house, craft breweries, dining options& golf all nearby. Escape Florida or Arizona summer heat!

4.95 out of 5 average rating, 20 reviews

An inviting dining area features a large wooden table surrounded by eight chairs. A modern kitchen with a stylish island and bar seating is visible in the background. Natural light fills the space through large windows, highlighting the warm wood accents of the vaulted ceiling.

Condo in Warren

Charming Sugarbush Farmhouse Condo with Hot Tub

MRT-11088676 The Mad House used to house the most exclusive restaurant in the valley. After a million dollar renovation it has transformed from the Common Man restaurant into the Mad House Rentals. This professionally managed, Renovated barn is nestled between Lincoln Peak and Mount Ellen, with Mad River Glen just a short distance away. The Mad House brings you everything you could want for any season. Ski lockers, mudrooms, A/C in most units, private decks with private grills and hot

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

4.95 out of 5 average rating, 19 reviews

Home in Enfield

Upper Valley Shaker-Style Home, close to Dartmouth

Located within minutes to Dartmouth Health Medical Center and Dartmouth College, this home offers a comfortable, warm place to gather with friends and family during your visit to the Upper Valley. Just off Route 4, this home offers easy access to I-89 and I-91. This home is unique in its location and proximity to Mascoma Lake. A common right of way and short walk will lead you to the lakefront park and rail trail, where the views are breathtaking. Snowmobile access to rail trail

5 out of 5 average rating, 10 reviews

A waterfront home is surrounded by lush greenery, featuring a large deck with multiple seating areas. A small blue paddleboat is visible on the lake, alongside a spacious dock equipped with Adirondack chairs. A calm, reflective water surface complements the serene environment.

Cottage in Croydon

Charming Lakefront cottage with beautiful views

Make memories with family or friends at our perfectly situated waterfront getaway. Enjoy the tranquility of waking up to peaceful mornings with a cup of coffee on your bedroom balcony. Take a leisurely tour of the lake in our kayaks or paddleboat. In the evenings, enjoy toasting smores on the camp fire. Our spacious dock is great for fishing or sitting in the Adirondack chairs with your favorite beverage. We look forward to offering our guests a vacation to remember.

4.97 out of 5 average rating, 33 reviews

A modern kitchen features wood cabinetry and stainless steel appliances. A polished countertop provides ample workspace, while a multiple-burner stove and microwave cater to cooking needs. Natural light enhances the room through a nearby window, complemented by patterned curtains. A trash can and sink are also visible.

Apartment in Pittsford

Norm's Place

Located in historic Pittsford Vermont, come stay in our newly renovated private unit. Close to Killington and Pico for skiing, the Mountain Top Inn , The Brandon Inn and Lilac Inn for weddings and events. Walking distance to the Pittsford Recreation center and walking trails. Convenient to swimming at the Chittenden reservoir or State Parks. Lots of opportunities for hiking and experiencing local breweries. Come see what our beautiful state has to offer!

4.96 out of 5 average rating, 225 reviews

A spacious wooden house features a balcony with a railing, overlooking a green lawn. Large windows allow natural light to fill the interior, while five skylights add brightness. Vibrant trees display autumn foliage in the surroundings, creating a serene atmosphere.

Home in Addison

Brthtkng New Premier Lake Champlain Wfrnt Escape!

7/19/20 : UPDATE - We are fully compliant with all local, state and federal safety protocols. Call /text Us fir any questions, at 978-502-6282 . Be Well, Be Safe & We Look Forward to Having You as Our Guests! We are the #1 Premier Lake Champlain Breathtaking New Property with 250'+ Prime Lake Champlain West/Sunset/Adirondack Mtn. facing w/Amazing Sunsets & Jacuzzi Tub in Master Bath Overlooking Lake,Mountains & Amazing Sunsets and 250+ 5 Star Reviews!

4.96 out of 5 average rating, 26 reviews

The kitchen features a modern design with white cabinetry and a wooden countertop. Two windows allow natural light to brighten the space, while stainless steel appliances, including an oven, are positioned along the walls. A sink is centrally located, enhancing functionality.

Home in Cavendish

3BR 1Bth New England Cape - Experience Vermont!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

4.78 out of 5 average rating, 9 reviews

Apartment in Warren

Professionally Managed Ski Gem

New listing! Come de-stress in the beautiful mountains of Vermont. Our condo and all the amenities included are perfect for a romantic getaway or a family vacation. Located less than a half mile from Sugarbush Resort, our condo is an ideal location for a ski vacation. However, the access to 3 pools, 2 hot tubs, tennis courts, basketball court, gym and more make this a perfect 4 season rental as well!

4.8 out of 5 average rating, 10 reviews

The vacation home features a multi-level structure nestled among trees, showcasing a rustic brick chimney and expansive windows. A spacious deck extends from the upper level, offering a view of the surrounding nature. The exterior is complemented by vibrant autumn foliage.

Home in Hartford

Pet-Friendly, Mountainside Home | Treetop Lodge

Our vacation home is the ultimate getaway for families and groups looking to indulge in luxurious comfort and endless entertainment options. Book your stay today and experience the beauty and tranquility of this truly remarkable property. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *Pet Friendly, fee applies per pet. *Includes Quechee Club Access

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Popular amenities for Stockbridge vacation rentals

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Stay near Stockbridge's top sights

Thundering Brook Falls Trail25 locals recommend

Green Mountain National Golf Course23 locals recommend

Clear River Tavern10 locals recommend

Gifford Woods State Park10 locals recommend

Original General Store11 locals recommend

Tozier's Restaurant3 locals recommend

Other great vacation rentals in Stockbridge

5 out of 5 average rating, 12 reviews

A stone pathway leads to a lakeside retreat, flanked by lush greenery and blooming hydrangeas. The tranquil waters of Lake St. Catherine are visible in the background, bordered by rolling hills under a clear blue sky.

Home in Wells

Breathtaking Lakeside Retreat!

5 out of 5 average rating, 9 reviews

A billiards room features a vibrant red pool table at its center, surrounded by wooden flooring. Natural light floods in through large windows, highlighting the contemporary decor. An antler chandelier hangs above, while colorful glass items are displayed on a sleek, white shelf against the wall.

Home in Bellows falls

Amazing Views, Skiing Nearby and Amenities Galore!

4.86 out of 5 average rating, 35 reviews

A spacious estate is surrounded by a pristine winter landscape, featuring snow-covered grounds and towering trees. The residence showcases a distinctive architecture, framed by distant mountains under a bright blue sky. The outdoor space invites exploration and enjoyment of the snowy scenery.

Home in Manchester

Your VT Dream House: Fireplace, Pool, Dogs

5 out of 5 average rating, 8 reviews

A warm hot tub is presented against a snowy landscape, surrounded by trees bare of leaves. The distant view of the reservoir is framed by the serene white of winter, inviting relaxation and tranquility.

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

5 out of 5 average rating, 16 reviews

A modern home is set amidst natural greenery, featuring a wood-paneled exterior. The structure showcases multiple oversized windows on each floor, allowing for ample light. Surrounding grass and trees create a serene environment, enhancing the sense of privacy and tranquility.

Home in Plymouth

Luxury Modern Cabin near Okemo & Killington

4.75 out of 5 average rating, 57 reviews

The exterior of a contemporary A-frame house is set amidst a forest, featuring a new deck with outdoor space. A pathway made of stones leads to the entrance, while sunlight filters through the surrounding trees, casting soft light on the facade.

Home in Jamaica

Green Mountain A-Frame with HOT TUB near Stratton

4.98 out of 5 average rating, 40 reviews

A spacious hot tub emits a soft blue glow in the dark, surrounded by mist. The area is accented with a wooden deck, and a staircase provides access to the tub. Soft lighting enhances the peaceful ambiance of the outdoor space.

Home in Warren

Private Home with Hot Tub 1 mile from Sugarbush