Stockbridge, VT Vacation Rentals

Discover vacation rentals, homes, and villas in Stockbridge, VT for an upcoming trip, whether for leisure or work. Every home is curated and professionally managed, offering more space, comfort, and flexibility for your trip. Along with premium amenities like 24/7 local support and high-speed Wi-Fi, many homes are equipped with features to suit different travel styles, group sizes, and budgets. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can earn and redeem points on every stay.

3 Vacation Rentals in Stockbridge

Killington Cabin, Hot Tub & Foliage Views!

Stockbridge, VT, US
3 Bedrooms 8 Guests
Sep 20 - 22
$432 night

Brand New Central A/C (2026) | Panoramic Foliage Views | 14 Mi to Killington | Updated 1900s Cabin | Secure Mountain Bike Storage | High-Speed WiFi | Pet Friendly Unwind in the private hot tub after a day on the slopes or trails, then wander to the river just steps away. This updated farmhouse sleeps 8 across 3 bedrooms — with a wraparound deck, wood-burning fire pit, 2 cozy living rooms, and fast fiber WiFi. Peaceful setting, 14 miles to Killington skiing and Woodstock. Dogs welcome! -- THE PROPERTY -- - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed & 1 twin bunk bed - Living Room: sleeper Sofa - Additional Sleeping: Pack n' Play CABIN LIVING: Smart TV, 2 living areas, wood-burning stove, propane stove, dining table, board games, piano, WiFi speakers, OTA Home, piano, yoga kit w/ mats, rollers, blocks, etc. OUTDOORS: Private hot tub, wraparound deck with dining table & chairs, en-suite balcony off Bedroom 1, yard with wood-burning fire pit, Adirondack chairs, and a gas grill. KITCHEN: Fully equipped, cooking basics, spices, dishware & flatware, knife set, drip/Keurig coffee maker, toaster oven, microwave, toaster GENERAL: Brand-new central air conditioning (2026), central heating, free high-speed fiber WiFi, tower fans, washer & dryer, towels & linens, self check-in via keypad, and driveway parking for 4+ vehicles, bike repair & air station FAQ: Ring doorbell security camera (1, facing driveway), stairs required for access, no cell service PARKING: Driveway (4+ vehicles) -- THE LOCATION -- HIT THE SLOPES: Pico Mountain Ski Resort (12 miles), Killington Ski Area (14 miles), Sugarbush Resort (31 miles), Okemo Mountain Resort (39 miles), Stratton Mountain Resort (63 miles) HIKING & BIKING: Green Mountain Trails (4 miles), Thundering Brook Falls Trail (10 miles), Appalachian Trail (10 miles), The Canty Trail (15 miles), Bucklin Trail (19 miles) GOLFING: White River Golf Course (6 miles), Green Mountain National Golf Course (7 miles), Killington Golf Course (14 miles), Montague Golf Course (19 miles) LOCAL ATTRACTIONS: Kent Pond (11 miles), Killington Adventure Center (14 miles), Norman Rockwell Museum of Vermont (19 miles), Wonderfeet Kids Museum (21 miles), Silloway Maple (25 miles) FARMS: Riverside Farm (3 miles), Kiss the Cow Farm (17 miles), Hathaway Farm (21 miles), Sleepy Hollow Farm (27 miles), Sugarbush Farm (29 miles) AIRPORT: Rutland Southern Vermont Regional Airport (27 miles) -- REST EASY WITH US -- Property Manager makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $75 fee (+ fees & taxes, max 2 pets) - No events, parties or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Tower fans are provided in all other rooms for cooling during the summer - NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed - NOTE: The property requires stairs for both home and bedroom access and may be difficult for guests with limited mobility - NOTE: Due to the rural location, guests may have weak cell phone reception in the area; however, there is high-speed WiFi in the home - NOTE: Guests are responsible for propane exchanges for the gas grill

Sunnymede Hill House with Hot Tub & Valley Views

Bethel, VT, US
4 Bedrooms 8 Guests
Sep 16 - 18
$1,389 night

Wake up to breathtaking Vermont views at Sunnymede Hill, where walls of windows flood every room with natural light and an open floorplan brings everyone together in style. Enjoy luxury amenities, including a private hot tub, piano, and modern kitchen, in a home designed for unforgettable gatherings and relaxation. Please see: Other Things to Note For Area Details, please see: The Neighborhood & Getting Around • This is a No pet property. Sunnymede Hill, Home Features: • 4 Bedrooms, 3.5 Baths, up to 8 guests • Walls Of Windows With Stunning Vermont Views • Gas Fireplace & Playful Piano • Parking in 2 Car Garage with 2 EV Chargers • Modern Kitchen With Breakfast Counter • Private Patio With Hot Tub • Free WiFi & Smart TV Welcome to Sunnymede Hill, where every sunrise, sunset, and starry night is on display, thanks to a home designed with more windows than you can count! Vermont’s spectacular scenery is always front and center here, as natural light pours into every corner, flooding each room with brightness and showcasing panoramic views you’ll never forget. From the moment you arrive, you’ll see why the windows, and the ever-changing landscape beyond, are truly the heart of this home, framing the breathtaking countryside and creating a cheerful retreat for up to eight guests. Whether you’re here for a family getaway, a friends’ reunion, or a work-from-anywhere adventure, this high-end, four-bedroom, three and a half bath home is ready to inspire. The magic of Sunnymede Hill is how its spacious, open floorplan brings everyone together. The living area, dining room, and breakfast counter flow seamlessly into one another, inviting connection and laughter throughout the day. Picture mornings in the breakfast counter, sipping coffee as sunlight streams through oversized windows and you watch the countryside wake up. Gather around the dining table for eight, perfectly placed beside patio doors that open to the backyard, or curl up on the plush sectional by the gas fireplace for cozy evenings and movie nights. The living area’s beautiful piano is always ready for a spontaneous singalong or to set the mood with a little music, adding a playful, joyful touch to your stay. One of Sunnymede Hill’s standout features is the serene tea room, a sunlit sanctuary designed for peaceful mornings, afternoon reading, or simply soaking in the ever-changing Vermont scenery. Surrounded by walls of windows and nestled next to an expansive but cozy window seat, this inviting space is perfect for enjoying a cup of tea, quiet reflection, or connecting with loved ones as you watch the landscape unfold outside. The tea room’s tranquil ambiance and natural light make it a favorite spot for relaxation and inspiration, capturing the essence of what makes Sunnymede Hill so special. The kitchen is a modern showstopper, featuring porcelain countertops, sleek black and white cabinetry, all stainless steel appliances, and counter seating for four. A clever pantry with additional access to the mudroom, along with a coffee bar and wine glass cabinet, offer thoughtful touches for both convenience and celebration, while the entire space is bathed in natural light from the home’s signature windows. The first upstairs bedroom is perfect for kids or guests, with two twin XL beds and a desk for school or remote work. The primary suite is a true sanctuary: a king bed, electric fireplace, sitting area with rocking chair, private glass-enclosed balcony, and a spa-inspired ensuite bath with a huge walk-in shower, soaking tub, dual vanities, heated tile floor, automated toilet with bidet and seat warmer, and its own balcony access, plus a dedicated desk for those who need to stay connected. The third queen bedroom offers a work desk and window bench, with three large windows framing the landscape. The fourth bedroom is a versatile Murphy queen room located just off the spacious downstairs bonus area. This level is designed for entertainment and relaxation, featuring a dedicated media theater with a 4K projector, a 100-inch ambient light rejecting (ALR) screen, a plush sectional perfect for movie nights, and a snack bar surrounded by fun movie posters for that true cinema experience. Right next to the media room, you’ll also find a convenient fitness area, ideal for keeping up with your workout routine during your stay. This flexible space is perfect for guests who want both comfort and a little extra fun. Step outside to your private patio and soak in the hot tub, where the views stretch for miles and every soak feels like a retreat. For your convenience, you can park right in front or inside the garage, where you’ll also find two EV chargers, perfect for electric vehicles and road trip adventures. On top of all of the amenities you’ll enjoy at Sunnymede Hill, you can also be a part of conserving the natural beauty of the Vermont landscape. The house is net zero due to an energy efficient design and solar power, and also has ample battery reserves for added peace of mind. At Sunnymede Hill, the windows invite the outside in, the open floorplan brings everyone together, and every detail is managed with care. As your Property Manager host, I’m here to ensure your stay is seamless, joyful, and truly memorable. Book your escape to Sunnymede Hill and experience Vermont’s best views, shared with the people who matter most, in a home designed for togetherness. This home uses keyless entry for self-check-in; your door code is sent by email and text within two weeks of arrival. Early check-in and late check-out are available upon request (subject to availability). Please contact us at least 24 hours in advance. Come and make unforgettable memories in this charming Vermont haven, we can’t wait to welcome you! The Upper Valley experience effortlessly weaves together Vermont’s natural beauty with the cultural vibrancy of nearby Hanover, creating a blend of outdoor adventure, historical exploration, and small-town charm. Whether you’re soaking in scenic wonders or exploring cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for relaxation and adventure in the Woodstock-Barnard area, where every moment is infused with classic New England charm. Nestled amidst breathtaking landscapes, our vacation rental offers unparalleled access to attractions and activities for every interest. Traveling To & Around the Upper Valley: • You’ll need your own car, as taxis are limited. While the town center is walkable, you’ll want to drive to nearby hikes and sightseeing spots. Outlying areas, like South Woodstock, are best accessed by car. • Bike rentals are available in the village, but biking in the commercial area is discouraged due to traffic. The terrain is hilly, mountain bikes are best for exploring the rugged countryside. Airports: • Burlington (BTV), VT • Lebanon (LEB), NH • Manchester (MHT), NH • Boston Logan (BOS), MA Popular Landmarks: • Mount Ascutney • Norman Williams Public Library • Woodstock Town Hall • Marsh-Billings-Rockefeller National Historical Park • New England Falconry • President Calvin Coolidge State Historic Site • Sugarbush Farm • Hanover, home to Dartmouth College Please pay close attention to following the house rules. Non compliance could result in sizable fines. • All guests staying at an Field and Farms Vacation Homes by Property Manager are required to sign (esignature) a rental agreement and complete identity registration. • Age restrictions apply. Reservation holder must be 25 years of age. • Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don’t hesitate to reach out to Field and Farm Vacation Homes by Property Manager directly. • Known damages incurred during your stay must be reported to the property manager immediately. • Before check in, we will send you detailed directions to ensure a seamless arrival. • Check-in time is 3:00 p.m. Check-out time is 10:00 a.m. • We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night. • Some homes have cameras for external monitoring only. • In the State of Vermont and in the Village of Woodstock, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. • This is a No Pets property. A daily rate fee of $150.00 will apply for violations and you may be asked to vacate the premises with no refund at the discretion of the Host. • This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.

Bear Foot Lodge

Stockbridge, VT, US
4 Bedrooms 12 Guests
Sep 16 - 18
$394 night

Bear Foot Lodge: Spacious Vermont Mountain Chalet Near Killington Resort and Riverside Farm Discover the perfect Vermont escape at Bear Foot Lodge, a stunning 5,000 sq ft post and beam chalet nestled in the scenic Green Mountains of Stockbridge. This custom-built home is less than 10 miles from world-class skiing and adventure at Killington Resort and just 3 minutes from the popular Riverside Farm wedding venue. Bear Foot Lodge is ideal for families, groups, and wedding guests seeking comfort, style, and convenience. Book with us and save on ski and snowboard rentals through our local partners. Guests also have access to a limited number of discounted Killington lift tickets. Step inside and be greeted by warm colors, modern art, and a blend of leather and wood that creates a contemporary ski lodge atmosphere with classic Vermont charm. The open-concept main level features a superb chef’s kitchen with Vermont Verde granite counters, slate flooring, and stainless steel appliances, making it easy to prepare group meals. Gather around the spacious dining table or relax in the beautiful living room, complete with a stone fireplace and a handsome log mantel. This is the perfect spot for cozy evenings after a day outdoors. Bear Foot Lodge offers four comfortable bedrooms and a unique third-level tree house loft that kids will love. The luxurious master suite includes a large walk-in rain shower for a spa-like experience. The lower walk-out level is designed for fun and relaxation, featuring a large recreation room with a fieldstone fireplace, a second kitchen, and a bathroom equipped with a sauna and jetted tub. This space is perfect for unwinding after mountain adventures. Enjoy your morning coffee or evening barbecue on the expansive wraparound covered porch with breathtaking mountain views. The outdoor space is perfect for grilling, dining, or simply soaking in the fresh Vermont air. Direct access to snowmobile, hiking, and biking trails means adventure is always just steps away. Additional amenities include fast WiFi, a smart TV for streaming, laundry facilities, and ample parking for multiple vehicles. Whether you are planning a ski trip, a summer hiking retreat, a fall foliage tour, or attending a wedding at Riverside Farm, Bear Foot Lodge offers year-round comfort and privacy in a beautiful mountain setting. Book your next Vermont getaway at Bear Foot Lodge and experience the best of Killington, Stockbridge, and the Green Mountains. Enjoy space, luxury, and the true charm of Vermont, all in one unforgettable home. - You understand use of the sauna is at your own risk and that special risks may be involved in using the sauna. You accept full responsibility for any bodily injury arising from use of the sauna, and hold owner and property manager harmless. - Please be sure that you have entered the correct number of guests as we may have a per-person per-night surcharge to cover expenses. You can contact us for a custom quote before booking. - Our minimum rental age is 25. - We will provide you with door codes for our smart locks to come and go as you please and for contactless check-in and out. - We have some flexibility around our standard check-in and check out times depending on other bookings. Guaranteed early check-in or late check-out may be available for an additional charge. - Our entire home is non-smoking (e-cigs included). You may only smoke on the outdoor deck. There is a $500 fine for smoking in the house. - You must e-sign and return our written rental agreement after you complete your booking. - For your safety and ours, we have a camera on the front of the house facing the driveway. There are no cameras inside the house. - Quiet hours are from 10 PM to 8 AM. We may use Minut, smart home technology that measures volume levels throughout the property and allows us to respond to noise nuisances without disrupting your stay. If you have any questions, please ask. We are committed to your comfort so please let us know if we can do anything during your stay to make it more enjoyable. - Fireworks are not permitted. - Please be advised that this property utilizes a ladder to access the bunk beds. By renting this property, you are agreeing to hold the owner and property manager harmless for any injury or death that is resulting from the use of the ladder. - Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended. SKI RESORTS: Killington Snowshed Base (12.5 miles), Killington K1 Base (13.1 miles), Pico Mountain (10.1 miles), Mountain Meadows Cross Country Skiing (8.1 miles) NIGHTLIFE: The Foundry at Summit Pond (11.8 miles), Pickle Barrel (12.0 miles), Wobbly Barn (12.2 miles) GOLF: Killington Golf Course (12.6 miles), Green Mountain National Golf Course (6.6 miles) WEDDINGS: Killington Grand Resort (12.6 miles), Mountain Top Inn Resort (17.3 miles) AIRPORTS: Rutland Regional Airport (21.7 miles), Burlington International Airport (71.5 miles), Albany International Airport (116 miles), Manchester-Boston Regional Airport (114 miles)

Vacation Rentals in Stockbridge by Amenities & Features

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Vacation Rentals Near Stockbridge

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