House vacation rentals in Londonderry

4.95 out of 5 average rating, 140 reviews

A serene scene features a spacious house nestled beside a tranquil pond. Vibrant autumn foliage enhances the landscape, with a mix of orange, yellow, and green trees lining the property. The grassy area invites exploration, while reflections on the water add to the peaceful ambiance.

Home in Grafton

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

4.95 out of 5 average rating, 323 reviews

The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.

Home in Weston

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

A cozy cabin is framed by lush gardens, featuring various flowering plants and shrubs in vibrant colors. A stone path leads to the cabin entrance, with greenery surrounding the area. Tall trees create a natural backdrop, enhancing the serene country setting.

4.93 out of 5 average rating, 115 reviews

VT Cabin sitting above the West River and Village

Converted in 1967 this 1 bedroom, 1 bathroom cozy cabin was once a tractor shed for the historical William's Mills along the West River. It now sits on 12 acres on a country dirt road overlooking the river and the Village. Amenities (stores, dining) are a 1-minute drive, and there are walking trails at the end of the road. It's a great Vermont getaway with ski mountains, Stratton, Bromley, and Magic just minutes away! Cross-country skiing, snowshoeing, and the VT Country store nearby!Yes, Wi-fi!

A welcoming living area features a stone fireplace with a warm fire glowing inside. Wooden beams cross the ceiling, and a red couch is complemented by leather ottomans. A large window reveals a snowy outdoor setting, while a coffee table holds various items.

4.85 out of 5 average rating, 205 reviews

The Mushroom House of Manchester Vermont

Welcome to The Mushroom House. Located at the end of a private road, the house is less than 4 miles from Manchester's outlet shopping, gorgeous hiking and unmatched dining. Our property features an open floor plan main floor with a kitchen, dining and living area that neighbors the master bedroom and bath. The back deck is a accented with string lights, a grill and comfortable outdoor furniture. Down stairs has two guest rooms with queens beds, a full bathroom and a den with full futon and tv.

4.87 out of 5 average rating, 120 reviews

A spacious living room features a textured red carpet and a large beige sectional sofa, complemented by a wooden coffee table. A stone fireplace is situated against one wall, with large windows providing views of the surrounding greenery. Decorative plants and artwork enhance the inviting space.

Home in Weston

4 Bedroom Family Ski House w/ WiFi, cable!

This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.

4.95 out of 5 average rating, 357 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

The exterior of a charming farmhouse is viewed, featuring white siding and a red front door. A large tree stands in the foreground, while green foliage and a stone path enhance the natural setting. A brick chimney is visible on the roof.

4.94 out of 5 average rating, 188 reviews

Clean, Captivating VT Farmhouse near Stratton!

Let us welcome you to our beautifully appointed, circa 1901 Vermont farmhouse resting on four acres of lush, rolling pastures--the quintessential Vermont experience! The house exudes warmth, coziness and tranquility with no detail left untouched. 4 BR 2 bath with huge family room. Minutes to 3 of the best ski-mountains on the east coast - Stratton, Bromley, Magic Mtn and close to Manchester shopping. A few miles from renowned Solo Farm & Table, HoneyPie and West River Farmer's market.

4.87 out of 5 average rating, 106 reviews

Home in Chester

Charming Chester Farmhouse Near VT Slopes

Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!

4.98 out of 5 average rating, 163 reviews

A charming home is shown, featuring a combination of wood and glass elements. The property is surrounded by green lawn and seasonal foliage. Rolling pasture views are visible in the background, lending a serene and open feel to the setting.

Home in Peru

Serene & Pristine Vermont Home

Perfect for a staycation, as a work-from-home alternative, or for family vacations. Situated on the edge of picturesque 120 acre New Spring Farm that borders the Green Mountain National Forest, is this up to date charming home awaiting your visit. With brilliant natural light and rolling pasture views, the quiet dead end dirt road provides privacy, while still being only a mile from J.J. Hapgood general store and centrally located to multiple towns and ski areas.

4.96 out of 5 average rating, 101 reviews

Home in Windham

Artistic Southern Vt Countryside Home at Windham

Escape to 3.5 private acres in the Green Mountains. Art-filled spaces, Tempur-Pedic beds, A/C, two living rooms, full kitchen with gas stove. Groomed trails and berry foraging outside your door. Fire pit with valley views. Minutes from waterfalls, swimming holes, the Appalachian Trail, and Londonderry dining. Magic Mountain under 10 min, 4 more ski areas nearby. Pellet stove, generator, dedicated workspace — perfect for remote work or a mountain reset.

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

4.99 out of 5 average rating, 151 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.

4.98 out of 5 average rating, 433 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Popular amenities for Londonderry house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 181 reviews

A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.

Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

4.96 out of 5 average rating, 140 reviews

Home in Springfield

Ski Mountain View Estate

4.98 out of 5 average rating, 213 reviews

The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.

Home in Salem

Historic Farm Stay | Heated Pool + Hot Tub

4.89 out of 5 average rating, 180 reviews

A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.

Home in Wilmington

Family-friendly 4BR | Pools Hot Tub | Near Mt Snow

4.93 out of 5 average rating, 249 reviews

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

The Brick House on Washington Street

4.9 out of 5 average rating, 143 reviews

Home in Colrain

The 1770 House

4.9 out of 5 average rating, 239 reviews

A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.

Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

4.88 out of 5 average rating, 280 reviews

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

Weekly house rentals

4.99 out of 5 average rating, 170 reviews

Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

An aerial view showcases the expansive outdoor deck of the Shred Shack, featuring a hot tub and a large dining table for outdoor meals. Sun loungers are positioned nearby, and the building's blue exterior offers a vibrant contrast with the surrounding greenery.

4.95 out of 5 average rating, 112 reviews

Shred Shack: A/C | Hot Tub | Sauna | EV charger

4.98 out of 5 average rating, 301 reviews

An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.

Home in Pownal

Cozy Vermont mini-house

An updated church building features a blend of shingle siding and architectural details. Large arched windows are visible, along with a distinctive spire above the entrance. Snow covers the surrounding area, which is framed by trees and a clear blue sky.

4.95 out of 5 average rating, 41 reviews

The Green Mountain Chapel

A modern chalet is set among snow-covered trees, featuring a spacious deck with a railing. Dark blue exterior walls contrast with white snow, while large windows provide views of the surrounding winter landscape. The sloped roof is lined with fresh snow, enhancing the serene atmosphere.

5.0 out of 5 average rating, 39 reviews

Modern Chalet: Magic Mountain

A warm living area features wood-paneled walls and a high-beamed ceiling. A brick fireplace serves as a focal point, accompanied by a flat-screen TV above. Comfortable seating includes a blue sofa, armchair, and a traditional rocking chair. Natural light streams through the windows, creating a cozy ambiance.

4.76 out of 5 average rating, 21 reviews

Close to 4 mnts. Private stream! King bed. Dogs OK

A charming Cape Cod home is set on a lush green lawn, framed by trees and flowering shrubs. Round hay bales are scattered across the field, complementing the inviting exterior. A cloudy sky adds a soft, natural light to the scene.

4.93 out of 5 average rating, 44 reviews

Spectacular 'Cape Cod' in Vermont!

The serene West River flows calmly alongside the property, framed by smooth stones and lush greenery. A spacious house is visible in the background, nestled among trees, with a deck overlooking the water, creating a peaceful natural setting.

4.97 out of 5 average rating, 36 reviews

Book Now For Leaf-Peeping!

Private house rentals

Home in South Londonderry

A charming treehouse sits elevated on wooden stilts, surrounded by lush greenery. Soft lighting decorates the deck area, creating a warm environment. A gravel path leads to the entrance, while the tranquil pond reflects the evening sky in the background.

Lovers Honey Pond Treehouse with hot tub & sauna

4.81 out of 5 average rating, 189 reviews

5.0 out of 5 average rating, 81 reviews

The living room showcases vaulted wooden ceilings and large windows offering expansive views of the outdoors. A cozy seating arrangement is positioned around a central coffee table, with warm lighting provided by a chandelier. Natural light fills the space, enhancing the welcoming ambiance.

Home in Andover

Luxury VT Retreat. Breathtaking Views & Sunsets

4.98 out of 5 average rating, 54 reviews

The exterior of the home is set amidst wooded surroundings, featuring a dark exterior with a vibrant pink front door. A gravel driveway leads to the entrance, surrounded by autumn foliage. The metal roof complements the natural scenery, enhancing the home's country charm.

Home in Jamaica

2-Bedroom Home, 7 Minutes From Stratton Mountain

4.83 out of 5 average rating, 24 reviews

A charming restored house with a distinctive pink exterior is framed by lush greenery. The front door is painted a vibrant teal, complementing the white trim and windows. A tall tree stands beside the home, adding to the serene outdoor setting.

Home in Grafton

Pettengill Schoolhaus scenic 2 min to main village

The exterior of a classic New England farmhouse is presented, featuring white siding and a gable roof. A welcoming front porch with decorative railings offers access to the main entrance, while the surrounding grassy area is complemented by trees in the background, indicating a serene rural setting.

5.0 out of 5 average rating, 15 reviews

Winterbee House

The image captures a spacious lodge nestled in a lush green landscape, surrounded by dense trees and rolling hills. Sunlight illuminates the vibrant foliage, and a clear blue sky with scattered clouds enhances the serene outdoor setting.

4.94 out of 5 average rating, 18 reviews

Cozy and Private Mountain Lodge

5.0 out of 5 average rating, 55 reviews

Home in Weston

West River Farmhouse in Weston, VT