Holiday rentals with outdoor seating in Montgomery

4.99 out of 5 average rating, 183 reviews

Cabin in Enosburg

The Rustic Retreat at Twin Ponds

Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away - you’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. When morning comes, enjoy your coffee while cozied up in front of the fireplace. Or simply stay in bed and admire the view. With plenty of land to explore, a hike is always welcome. The choice is yours!

5 out of 5 average rating, 163 reviews

A serene outdoor space features a patio table surrounded by chairs, set against the calm waters of Metcalf Pond. A large umbrella provides shade, while an American flag gently flutters nearby. The backdrop includes rolling hills adorned with autumn colors.

Cottage in Fletcher

Metcalf Pond Camp Convenient to Smugglers Notch

Handcrafted cozy waterfront camp on Metcalf pond. Propane fireplace provides for welcome warmth after fall or winter adventures. Soak in the Hot tub on the deck. Custom spiral staircase accesses carpeted sleeping loft with books, TV, rocking chair. Enjoy the quiet off season brings to the area when most camps are shuttered for winter. Enjoy staying in and cooking and taking in the cozy atmosphere or make the approximately 20 minute drive to Smugglers Notch or enjoy other local attractions.

4.96 out of 5 average rating, 137 reviews

A blue house with a pitched roof is set against a clear blue sky. Lush green grass surrounds the property, and trees provide a natural border. A person is seen walking across the spacious lawn, highlighting the outdoorsy setting.

Home in Montgomery

Hillwest Mountain View

We are close to Jay Peak and Canada including Montreal. If you like hiking, the Long Trail is close by. If you like star gazing you will love seeing the Milky Way in our backyard. Our house is good for both couples and families. We have a private hiking trail that leads down to a cool mountain stream where you can cool off. Take a dip in the nearby Hippie Hole or go fishing or canoeing in nearby lake Carmi. There are three bedrooms and a master bath with a spa tub. Wifi, fireplace and more.

4.97 out of 5 average rating, 285 reviews

A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.

Treehouse in Newport

Secluded Luxury Treehouse - Hot Tub + Projector

Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

4.94 out of 5 average rating, 126 reviews

A green two-story house is viewed from a snow-covered path leading to its entrance. Thick layers of snow blanket the yard, while tall trees stand in the background against a clear sky, indicating a serene winter setting.

Chalet in Montgomery

Montgomery Meadows Chalet near Jay Peak

Located on beautiful, historic Hazens Notch Road, Montgomery Center, Vermont. This “hidden gem” of a house sets back from the road in a private setting on 5 spectacular acres of cleared land, with views of Jay Peak Ski and Golf Resort. A perfect location for skiing, hiking, biking, golfing, etc. Only 15 minutes from the resort and all of the great amenities (water park, ice rink, movie theater, climbing wall, arcade). Only 3 miles from local amenities (grocery store, top rated restaurants).

5 out of 5 average rating, 281 reviews

A wooden picnic table is situated near a gently flowing river, surrounded by lush greenery. Large rocks are visible along the water's edge, and trees provide a natural backdrop under a partly cloudy blue sky.

Home in Montgomery

Trout River Lodge - Discount Jay Peak Lift Tix

Welcome to the Trout River Lodge! Check out the “Three Holes” swimming hole and waterfalls, just a few hundred yards up the river. We are located right in the heart of Montgomery Center, VT. Live music at the Snowshoe Pub, breakfast at Bernies, and groceries from Sylvester’s are all just steps away. You can also enjoy the mountain biking and hiking trails just minutes away! ***Discount vouchers for Jay Peak Ski. Price info can be found in the Photos section. It changes each year***

4.98 out of 5 average rating, 103 reviews

Cottage in Montgomery

Crofter's Green @ Jay Peak: O'Shea Farmhouse

The O'Shea Farmhouse is one of five micro-cottages at Crofter's Green - our small, thoughtfully-designed lodging property in the heart of Vermont. This cozy woodland retreat is just minutes from Jay Peak Ski Resort and the warm, eclectic town of Montgomery Center. this bright 2-story cottage sits at the forest's edge and offers a peaceful home base for exploring the Northeast Kingdom. It's simple, comfortable, and surrounded by nature. Find us on social media! @croftersgreen

4.95 out of 5 average rating, 152 reviews

A modern living area features a comfortable brown sofa beside a wooden coffee table. Exposed wooden beams run across the ceiling, while a staircase leads to an upper level. Natural light fills the space through large windows, creating a warm and inviting environment.

Cabin in Montgomery

Jay Peak Retreat

The Jay Peak Retreat – Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This warm, stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski lounging. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, patio, fire pit, and plush outdoor chairs. Just 1 hour from Burlington, 2 from Montreal, and 3.5 from Boston.

Apartment in Montgomery Center

The entrance features a vibrant red door framed by an elegant oval design, accompanied by inviting porch railings. Flowering plants and gravel decorate the pathway, while wooden signs highlight nearby services. The facade reflects a blend of modern charm and rustic warmth.

4.83 out of 5 average rating, 110 reviews

Light & cozy Jay Peak vacation apartment.

The Coach House was the original hotel for the area but has been converted into a boutique vacation rental in the foothills of Jay Peak. You will enjoy the comfort, convenience and affordability of being in the heart of a quaint Vermont town but only 10 - 12 minutes from world class ski slopes in winter, 5 golf courses within 30 minutes, great hiking, fishing, paddling and more.. It makes for a wonderful place to create vacation memories to last a life time.

5 out of 5 average rating, 160 reviews

A rustic cabin with a wooden exterior is surrounded by lush greenery. The inviting porch features several rocking chairs and is accessed by steps from a grassy area, while a gravel driveway leads to the entrance, enhancing the private setting.

Cabin in Wolcott

Meadow Woods Cabin, private, cozy and unconnected

Enjoy beautiful sunsets from your rocking chair on the cabin's wonderful porch. There is a large, well equipped kitchen, open space floor plan, new shower unit and plenty of closet space in the bedroom. Easy access to VAST snowmobile trails, within an hour's drive to 3 ski areas (Stowe, Smuggler's Notch and Jay Peak), X-Country skiing right outside the door or in Craftsbury or Stowe. Elmore State Park is 3 miles away. Hiking trails and kayaking abound!

4.96 out of 5 average rating, 236 reviews

A spacious living area features large windows allowing natural light to fill the space. A wood stove is positioned beside a modern, blue sofa. A dining table with green chairs occupies the center, complemented by wooden cubes that serve as additional seating.

Chalet in Sutton

Le chalet des bois, Peace and calm in the woods

*$* WINTER PROMOTION *$* For a weekend reservation (Fri. & Sat.) the 3rd night on Sunday is $90.00!. Monumental open concept, in the heart of nature. Access to trails directly behind the house. Wood stove, large modern bathroom, one bedroom + sofa bed. Another sofa bed in the living room. Ideal chalet for a couple with children or two couples. Wild birds, turkey, and deer lovers welcome! Wifi and EV charger included. Dogs Welcome! CITQ : #308038

4.92 out of 5 average rating, 512 reviews

An aerial view captures the tiny house nestled within lush greenery, surrounded by a gently winding river. Canoes and kayaks are visible near a private access point, while a serene landscape of trees and water reflects the tranquility of the setting.

Tiny home in Mansonville

Charming Tiny House by the water

Discover our charming Tiny House, ideal for a cozy stay by the river. Enjoy trails on the site and private access to the water. This project, lovingly designed, reflects our happiness to have a safe haven to recharge and practice outdoor activities. We want to share this experience with those looking for a sweet moment of wellness in the countryside. Treat yourself to a moment of serenity, alone or in love, in our little cocoon.

Popular amenities for Montgomery outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.94 out of 5 average rating, 100 reviews

A single-story house is framed by lush greenery and a clear blue sky. The front deck is accessible from a winding gravel driveway, with neatly trimmed bushes bordering the yard. Large windows invite natural light into the living space.

Home in Craftsbury

Relaxing Craftsbury Retreat

4.92 out of 5 average rating, 157 reviews

Home in Eden

SKI JAY & BOARD Lake Eden |Hot Tub|Wifi|Games|Pets

4.99 out of 5 average rating, 156 reviews

A serene winter landscape displays gently rolling snow-covered hills, with distant mountains rising under a clear blue sky. Small structures are scattered across the meadow, surrounded by sparse trees, creating a peaceful and open atmosphere.

Home in Richford

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

4.91 out of 5 average rating, 125 reviews

A charming chalet is set amidst greenery, featuring a welcoming front porch with seating. Two bright blue Adirondack chairs are placed near a fire pit on the lawn. A parked car is visible in the gravel driveway, surrounded by trees.

Home in Dunham

Lac Selby Chalet & Spa

4.99 out of 5 average rating, 148 reviews

The single-story home features a modern wooden exterior with large windows that allow natural light to enter. A spacious deck is equipped with outdoor seating and leads to a grassy area surrounded by trees. The inviting structure presents a blend of warmth and contemporary design.

Home in Starksboro

Forest Hideaway

4.88 out of 5 average rating, 177 reviews

A rustic exterior of the Sugar House is visible, showcasing a deep red facade. The building features multiple windows allowing natural light, with a stone chimney prominently located on one side. Lush greenery and a small stone pathway surround the structure, enhancing its natural setting.

Home in Johnson

The Sugar House, Maple Hill Road

4.99 out of 5 average rating, 172 reviews

A quaint guest home is nestled amid a snowy landscape, surrounded by bare trees and low shrubs. The property features a metal roof and a spacious porch, providing scenic views of the distant, snow-covered mountains.

Home in Waterville

4CR Farm Guest House 4 Season Vacation Destination

4.95 out of 5 average rating, 199 reviews

A countertop coffee station is displayed against a wall with a subtle floral pattern. The setup includes a coffee maker, a tray with creamers, and neatly arranged cups on shelves above. Below, a cabinet offers storage space, complementing the cozy kitchen environment.

Home in Irasburg

Lord’s Creek Private Haven

Apartment rentals with outdoor seating

4.96 out of 5 average rating, 205 reviews

The kitchen features wooden cabinetry with a granite countertop. Appliances include a black microwave, stove, and refrigerator. A window with lace curtains allows natural light to enter, while a coffee maker and bowls are placed on the countertop.

Apartment in Jay

Across from Tram Side Entrance of Jay Peak Resort

4.85 out of 5 average rating, 693 reviews

A spacious bed is framed by reclaimed barn wood walls, complemented by a decorative cushion and a soft gray blanket. Plush white linens are neatly arranged, with rolled towels displayed on the bed. A warm lamp illuminates the cozy sleeping area, near a large window.

Apartment in Stowe

Stowe Charm in South Village

4.96 out of 5 average rating, 165 reviews

A cozy studio space is shown, highlighting a gray dresser and a red chair with a patterned cushion. The open kitchen area is visible in the background, featuring shelving with kitchen items, a small dining table, and modern appliances, all under soft lighting.

Apartment in Montpelier

Contemporary Studio in Montpelier

4.98 out of 5 average rating, 251 reviews

A charming duplex style house is set against a backdrop of snow-covered trees and a clear blue sky. A path through the snow leads to the house, which features large windows and a welcoming entrance. Nearby, a rustic shed complements the serene winter landscape.

Apartment in Morristown

"Hot Tub Hideaway: Private Hot Tub, 9 min to Stowe

Apartment in Saint-Étienne-de-Bolton

A serene landscape features a large pond surrounded by lush greenery and trees. The natural setting illustrates the peacefulness of Ch’i Terra, while a spacious stone house is seen in the background, complementing the tranquil environment.

4.96 out of 5 average rating, 226 reviews

CH'I TERRA gîte-ressourcement between lake and river

Apartment in Jeffersonville

4.94 out of 5 average rating, 116 reviews

The Bootlegger Outlaw Hideout @The Pony Farm Ranch

4.99 out of 5 average rating, 237 reviews

A wooden bench with a decorative wrought iron back is positioned in front of a sign reading 'The House of the Setting Sun.' Lush greenery surrounds the bench, and a small rabbit is situated nearby, creating a peaceful outdoor scene.

Apartment in Newport

The House of the Setting Sun, Private Apartment

4.92 out of 5 average rating, 192 reviews

A spacious kitchen area features modern appliances, including a stainless steel refrigerator and a sleek island with a built-in sink. The contrasting orange accent wall adds a vibrant touch, while natural light floods the room through large windows.

Apartment in Philipsburg

4 1/2 Loft-style accommodation next to Lake Champlain

Condo rentals with outdoor seating

The kitchen features modern white cabinetry and stainless steel appliances. A spacious island with seating for four enhances the area. Pendant lights provide ambient lighting, while a window offers a view of the outdoors, complemented by warm wood flooring.

4.94 out of 5 average rating, 277 reviews

One level condo in the heart of Stowe Village!

A spacious studio features large windows with views of the outside landscape. A king-sized bed with a patterned duvet occupies the center, complemented by a queen sleeper sofa. A small table and chairs, along with a stylish armchair, create a comfortable seating area.

4.96 out of 5 average rating, 103 reviews

3rd Floor Studio @ The Lodge at Spruce Peak

4.95 out of 5 average rating, 175 reviews

A cozy living area featuring a grey sofa adorned with orange cushions. A natural wood coffee table occupies the center, while a mountain-themed wall art piece is prominently displayed in the background. Light enters through sliding glass doors leading to a private deck.

Condo in Cambridge

Lovely Ski-in / Ski-out Studio at “Smuggs”⭐️

An aerial view captures a modern farmhouse-style condo surrounded by trees with vibrant autumn foliage. The property features a wide deck, outdoor space, and a gazebo to the side, complemented by a manicured lawn and gravel pathway leading to the entrance.

4.97 out of 5 average rating, 142 reviews

Renovated 4-bedroom House: Hot Tub & Outdoor Space

The modern kitchen features stainless steel appliances, including a refrigerator and microwave. A sleek countertop with a unique wooden base is complemented by open shelving showcasing decorative items. The space is well-lit with natural light and offers a dining area with black chairs.

4.86 out of 5 average rating, 120 reviews

Newly Renovated 2 Bedroom Condo centrally located

4.97 out of 5 average rating, 214 reviews

A wooden deck features a small dining table with two stools, shaded by a large umbrella. Vibrant autumn leaves surround the area, reflecting in the nearby ecological lake, creating a serene outdoor setting.

Condo in Bolton-Est

Gîte des Arts

4.97 out of 5 average rating, 114 reviews

A serene exterior view showcases the apartment against a backdrop of a soft morning sky, where hues of pink and purple blend. Lush greenery and blooming flowers frame the yard, enhancing the peaceful rural setting.

Condo in Westfield

Northeast Kingdom Little Piece of Heaven