Vacation rentals in Middlesex

4.92 out of 5 average rating, 360 reviews

A wooden deck features a dining table surrounded by chairs, set among lush greenery. A six-person hot tub sits nearby, with steam rising gently. String lights create a warm ambiance, illuminating the tranquil outdoor space during the golden hour.

Cabin in Stowe

The Canopy House—Remodeled Vermont A-Frame Near Downtown

Awarded as one of the top Airbnb's in New England by Condé Nast and Boston Globe! Featured on multiple global publications. Watch the snowflakes fall from the comfort of the 6-person outdoor hot tub, with first-class stargazing to be had all year long. Back inside, the vaulted interior features OM Home Furniture, while a 50” TV with soundbar sits above a real fire. Less than a two mile drive to all downtown Stowe has to offer. 3 BD 2 BA modern A-Frame with two living rooms, 6 person hot tub, Fireplace, two new Roku TV's , soundbar, AC unit, WiFi, deck and back patio, rainfall shower, high-end mattresses, Sonos speaker and furnished by OM Home Furniture. Close to Main Street, 5 miles to Von Trapp, 9 miles to Stowe Mountain Resort and .5 miles from rte 100 to get you easily in and out of town. you will have access to entire house accept for one personal closet in back downstairs bedroom. Less than a 2-mile drive to downtown Stowe, this home is on a hill just off Route 100. Nearby Von Trapp is full of restaurants and other amenities. Ski and snowboard from Stowe Mountain Resort 9 miles away, with picturesque hiking in the summer. I would highly recommend a four wheel or all wheel drive vehicle. House is on a hill with a pretty steep road leading to it.

4.96 out of 5 average rating, 102 reviews

A cottage is seen perched on a grassy bank, overlooking a river. Tall trees frame the scene, providing a natural backdrop. The water's surface reflects the surroundings, while a hint of light is visible from the cottage window, suggesting warmth inside.

Home in Willsboro

"Beau Overlook" Enjoy 2 states from 1 great spot!

Come enjoy LOGISTICS to the Green Mountains of VT & the heart of the DACKS in one sweet spot. "Beau Overlook Cottage" perched high on the banks of the BOQUET RIVER, with sweet sounds of water tumbling over river rocks below. This home is situated 2 miles north of the Lake Champlain ~ Boquet River Delta. The beautiful LAKE scene at the sandbar of the delta must be seen to be appreciated. This relaxing sanctuary will provide an upscale and sophisticated home, whose logistics cannot be beat!

4.98 out of 5 average rating, 61 reviews

A spacious townhome in a picturesque neighborhood is shown with a gentle autumn backdrop. The property features a covered porch with white railings, surrounded by neatly trimmed bushes and trees with yellow leaves. A clear blue sky complements the inviting exterior.

Townhouse in Stowe

Stowe Depot townhouse - Fireplace -Deck- Rec Path

Spacious Stowe Village townhouse, in walking distance to many shops, restaurants and Park. The Main suite has a King bed, 40" HDTV, and an en-suite bathroom with Jacuzzi tub. The second bedroom has a queen bed, 27" HDTV and an en-suite bathroom. Beautiful kitchen with granite counters, coffee maker and grinder. Living room features a gas fireplace, smart TV and nice furniture. There is a comfortable Murphy bed and an air mattress for additional guests, plus a nice covered deck to enjoy!

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.

4.93 out of 5 average rating, 140 reviews

A modern lakefront home is showcased at dusk, highlighted by warm exterior lighting that illuminates the spacious deck. The inviting outdoor area features comfortable seating, while the surrounding nature adds a serene touch to the cozy atmosphere.

Home in Eden

Cozy Lake Eden Retreat|Hot Tub|Wifi|Games|Pets OK

Enjoy a quintessential Vermont getaway at this lakefront home. It’s the perfect place for remote workers and families looking for a perfect base for outdoor activities. Relax in then hot tub & admire gorgeous lake views, and enjoy direct access to the water. Rainy days are no less fun, with a game room and fireplace to keep you busy. Lake Eden –Frontyard! Eden Ethical Dog Sledding – 8 Min Drive Stowe – 30 Min Drive Create Lasting Memories In Eden With Us & Learn More Below!

4.97 out of 5 average rating, 36 reviews

A wooden deck with railings leads down a slope to the shale waterfront of Lake Champlain. The calm water reflects the greenery surrounding the area, creating a serene environment. Nearby, gentle waves can be seen lapping against the shore.

Cottage in Alburgh

#11 Isle View - Fishing, Sunsets, Beaches, Golfing

Located on Lake Champlain, this cottage has spectacular lake and sunset views. Perfect for relaxing, fishing, water sports, golfing, and also to use as a home base for fun day trips. Enjoy the sunroom which overlooks the beautiful lake, the nearby Alburgh Sand Dunes State Park and Alburgh Golf Links, and St. Anne's Shrine and the ancient coral reefs on Isle LaMotte. Dogs are welcome, but require Owner approval and payment of a $85 per dog per trip fee, maximum of 2 dogs.

5 out of 5 average rating, 7 reviews

The exterior of a two-story condo is surrounded by snow, showcasing a sloped roof and a welcoming red door. Bare trees provide a natural backdrop, with a glimpse of the mountain visible in the distance. Soft snow blankets the ground, creating a serene atmosphere.

Apartment in Jay

Absolute best ski on/off at Jay.

Location, location, location. This 2br Slopeside condo is position A on the snowiest mountain in the east. Inside, you'll find 2 bedrooms featuring a queen bed and a twin over full bunk. The kitchen comes fully equipped to make meal prep a breeze. The cozy living room has a gas fireplace to warm up or relax and enjoy an après drink. Our condos always feature complete linens, towels, and essential sundries because no one wants to lug that stuff to their vacation.

5 out of 5 average rating, 56 reviews

A spacious great room features floor-to-ceiling windows offering views of the green mountains. A cozy seating area surrounding a fireplace invites relaxation. A side table holds decorative items, while a wooden dresser adds functionality. Natural light enhances the welcoming atmosphere.

Home in Cambridge

Sunning Home near Smuggs/Stowe & Wedding Venues

Welcome to the Mirador- our Vermont getaway! Escape to the picturesque beauty of Vermont and indulge in a memorable stay at our charming retreat. Located just a stone's throw away from Smugglers Notch and conveniently close to popular wedding venues, this inviting house provides a comfortable and convenient base for your adventures. With its charm, modern amenities, and breathtaking surroundings, it's the ideal place to relax and explore all that Vermont has to offer.

Apartment in Waterbury Center

A covered outdoor seating area features a glass-top table surrounded by two black chairs. In the background, lush greenery and a serene lake are visible, with mountains rising in the distance under a blue sky scattered with clouds.

4.98 out of 5 average rating, 63 reviews

Sir Richards Waterbury Stowe 2 B Lake View Escape

A fun, filled, peaceful property surrounded by nature. Drift into an amazing, relaxed state sitting on the front deck listening to the water fountains & closeness to nature. Only the mountains, ponds, woods & lake on your side and in front of you. And yet, only 2 blocks from busy Route 100 attractions. Spacious 1200 sq. ft. 4 prs. snowshoes winter, 2 kayaks, & a canoe on the 6 1/2 mile Reservoir. Hiking & fishing summer & winter. "Memories Are Made Here."

4.88 out of 5 average rating, 317 reviews

A cozy loft bedroom features a wooden ceiling with exposed beams. A spacious bed is positioned centrally, flanked by two bedside lamps on dark nightstands. Light filters through a window adorned with curtain panels, illuminating the rustic wooden walls and framed artwork.

Cabin in Woodsville

Cabin Getaway, Pool Tb, Darts, Poker Tb, ATV Trail

Log cabin getaway in White Mountains, NH. Located in Mountain Lakes community, it is a perfect location from which to enjoy outdoors. You can fish, swim, hike, ski and then come back to a comfortable home. Sit on the deck and pick at the mountains or enjoy a get together by the big fire in the yard. Easy walk to the lakes. Close to trails for ATV and snowmobiles. Visit nearby towns of Lincoln, Littleton, Franconia with lots of restaurants and activities.

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!

4.89 out of 5 average rating, 167 reviews

Townhouse in Stowe

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

This beautiful Resort Condo is located in the award-winning, Top Notch Resort & Spa. Our spacious 2-bedroom, 2-bathroom condo is only 1 mile away from Stowe Mt. Resort while offering privacy and room to spread out on the resort’s 120 acres. It is perfect for families or couples. We are proud of our stellar reviews and competitive pricing. Newly updated, our home is ready for your perfect vacation! Enhanced Cleaning protocols in place!

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Popular amenities for Middlesex vacation rentals

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Pool

Free parking on premises

Air conditioning

Stay near Middlesex's top sights

Three Penny Taproom102 locals recommend

Hunger Mountain Coop station82 locals recommend

Sarducci's77 locals recommend

Positive Pie76 locals recommend

Michael's on the Hill68 locals recommend

Hubbard Park55 locals recommend

Other great vacation rentals in Middlesex

4.98 out of 5 average rating, 56 reviews

A view of a private dock extending into a calm lake under an overcast sky. Two figures can be seen at the end of the dock. Lush greenery borders the water, and wooden chairs are positioned on the grassy area, creating a serene outdoor setting.

Cottage in Derby

On Golden Lake Salem

5 out of 5 average rating, 52 reviews

Home in Plattsburgh

Entire New Lake House, private deck, large lawn

4.95 out of 5 average rating, 21 reviews

A serene outdoor space features a relaxing hammock, under a canopy of trees, overlooking the calm river. A barbecue grill and seating area are positioned nearby, providing a comfortable setting for outdoor gatherings amid gentle greenery.

Cottage in Champlain

Waterfront Kayak and relax on Great Chazy River

4.8 out of 5 average rating, 15 reviews

A serene view of MacIntosh Pond is framed by tall trees and lush greenery. The still water reflects the surrounding foliage, creating a peaceful atmosphere. Sunlight filters through the branches, illuminating the scene with soft natural light.

Cabin in Barnard

Private post & beam log cabin on Macintosh Pond.

4.82 out of 5 average rating, 45 reviews

A well-maintained garden is visible adjacent to the villa, featuring a stone pathway that winds through lush greenery. The sky showcases a mix of clouds and blue hues, creating a serene backdrop. The villa’s exterior is highlighted by both brick and siding elements.

Villa in Stowe

Beautiful 5 Bedroom Villa with Amazing Views

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

4.81 out of 5 average rating, 26 reviews

The living area features wood-paneled walls and high ceilings, illuminated by natural light from multiple windows. A comfortable couch is complemented by decor pillows, and a television is mounted on a wall. A woven rug lies on the wooden floor, contributing to a cozy ambiance.

Cabin in Peru

Adirondack Mountains Log Cabin