Are there pet-friendly vacation rentals in Middlesex?

Four-legged friends are welcome in Middlesex. Choose from more than 40 vacation rentals for guests traveling with pets.

How much does it cost to stay in apartment rentals in Middlesex?

Experience the best of Middlesex with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do house rentals in Middlesex have free parking?

Absolutely! We offer over 70 house rentals with free parking in Middlesex. Enjoy a tailored experience with all the comforts you desire.

Do apartment rentals in Middlesex have a kitchen?

Absolutely! We offer over 30 apartment rentals with a kitchen in Middlesex. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for Apartment Rentals in Middlesex?

Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with wifi, over 20 homes with air conditioning, over 30 homes with a kitchen, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Do apartment rentals in Middlesex have air conditioning?

Absolutely! We offer over 20 apartment rentals with air conditioning in Middlesex. Enjoy a tailored experience with all the comforts you desire.

Do apartment rentals in Middlesex have wifi?

Absolutely! We offer over 30 apartment rentals with wifi in Middlesex. Enjoy a tailored experience with all the comforts you desire.

Are there vacation rentals with a dedicated workspace in Middlesex?

Yes! Work meets play with ease at over 60 vacation rentals in Middlesex featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Middlesex

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middlesex

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A vibrant red barn is framed by greenery, with a full rainbow arching across a darkening sky. The barn's luminous white roof contrasts with the moody backdrop, creating a serene countryside image.

Barn in Middlesex

4.97 out of 5 average rating, 236 reviews

Jules Gem

Reconditioned Barn Apartment. One large room with 4 large windows creating much natural light with kitchenette, no oven at this time, but there is a toaster oven & BBQ Grill for your use Overlooking Mountains and situated next to a river. Enjoy the sounds and views of country on this 90 acre property. All new amenities and full bath with shower. Private swimming hole on property, steps from sought after hiking, 12 minutes to downtown Montpelier with fine dining, bars and unique shopping.

Top guest favorite

The yurt is shown nestled among vibrant autumn foliage, with colorful leaves in various shades surrounding it. The exterior features a tan roof and maroon walls, set against a clear blue sky. A winding path leads through the lush grass, inviting exploration of the natural landscape.

Bungalow in Worcester

4.97 out of 5 average rating, 696 reviews

Beautiful 30ft Yurt in the Green Mountains!

Gorgeous 5 STAR 30-ft yurt. The wrap-around deck looks out to the Worcester Range, trails leading from the yurt to babbling brooks. This charming space includes a fully equipped kitchen and a private bathroom with a claw foot tub/shower. Two queen beds, air mattress & futon mattress. 12 mi. to Montpelier and 7 mi. in the opposite direction to Lake Elmore, 4 miles to Worcester Trailhead and 6 miles to Hunger Mt! A beautiful sanctuary for peace and quiet or Netflix and Wifi, your hearts desire!

Top guest favorite

Aerial view of the vibrant Vermont landscape, showcasing rolling hills adorned with a diverse palette of fall foliage. The rustic barn sits among expansive fields, framed by trees displaying bright autumn colors, with distant mountains in the background under a partly cloudy sky.

Barn in Morristown

4.98 out of 5 average rating, 168 reviews

200 acre Stowe area Bunkhouse.

Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

Guest favorite

The exterior of a charming cabin is surrounded by snow-covered trees and a blanketed yard. A bold red door contrasts with the dark wooden facade and multiple windows, inviting entry. The peaceful winter setting emphasizes the cabin's rustic charm.

Cabin in Worcester

4.97 out of 5 average rating, 241 reviews

the little house

Come rejuvenate in our sweet little cabin tucked into the Vermont mountains. It has such wonderful healing energy! ✨ Cozy up to read a book next to the fireplace or book a private healing session at my studio in Montpelier, VT. I have a passion for creating welcoming, safe spaces that support your nervous system & empower your soul. ❤️ -On site Minister Brook access--5 min. walk -Lots of skiing, hiking, water to explore -18 min to Montpelier- funky downtown, eccentric shops & restaurants

Guest favorite

An exterior view of a contemporary home features large windows allowing natural light in. A spacious deck is adorned with a dining set, shaded by a dark umbrella. Lush greenery surrounds the property, offering a serene atmosphere.

Home in Waterbury Center

4.99 out of 5 average rating, 143 reviews

Stunning Views near Stowe / Private mountain home

Retreat and relax at this incredibly located and uniquely designed home nestled in the heart of ski country. This three bedroom, two bathroom vacation home is perfect for families or couples looking to enjoy Vermont's beauty and recreation. Very private location yet close to the amenities of Waterbury, Stowe and Mad River Valley. Enjoy the hiking trails, minutes away from this cozy home or the nearby ski slopes of Stowe. Sweeping views of the mountains throughout the house. Serene and lovely.

Top guest favorite

A circular fire pit is surrounded by three rustic wooden benches, positioned on a grassy area among lush trees. Two adults and a child sit comfortably, enjoying the warm glow of the fire. Behind them, the unique treehouse structure, with large windows, blends into the natural setting.

Treehouse in Moretown

5 out of 5 average rating, 102 reviews

4-Season Treehouse @ Bliss Ridge; Best Views in VT

thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Equipped w. a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

Top guest favorite

A sweeping view of autumn foliage showcases vibrant colors in shades of red, orange, and yellow. The mountainous backdrop is partially shrouded in gentle clouds, with an expansive green field in the foreground, creating a serene natural landscape.

Guest suite in Waterbury Center

4.96 out of 5 average rating, 274 reviews

Farmhouse with Sunset Mountain Views

Unbeatable Vermont setting, panoramic mountain views and gorgeous sunsets. Located one mile off Rt 100, 18 minutes to Stowe, minutes from the best skiing, bike trails, kayaking, and hiking in the east. The apartment is a sunny, bright and private space, cheerfully decorated, with the comfiest beds and coziest linens. And great outdoor spaces to relax in at the end of the day! 10 min to Stowe, 18 to lifts, 30 to Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!

Guest favorite

A cozy sitting area features a couch and an armchair, complemented by decorative cushions. Wall art is displayed above a television, and a kitchenette is visible in the background. Warm lighting enhances the inviting atmosphere in this thoughtfully arranged space.

Guest suite in Waterbury Center

4.93 out of 5 average rating, 460 reviews

Waterbury Center Guest Bedroom - 244 Howard

The guestroom room has a separate entrance located off a covered, back porch with a small table and chairs for summer use. There is adjustable heat and cool air from the wall mounted air-source, heat pump. The little kitchen alcove is convenient for coffee or tea or a light meal (toaster oven, single induction “hot” plate, water heater) We live in a historic building. Our neighborhood is very close to Rte 100. Waterbury village and Stowe are nearby too with skiing, hiking and biking.

Top guest favorite

The cottage, featuring a wooden exterior and large windows, is surrounded by greenery and natural rock formations. A stone pathway leads to the entrance, which is sheltered by an overhanging roof. Sunlight illuminates the peaceful setting, highlighting the rustic charm of the structure.

Guesthouse in Waterbury Center

4.99 out of 5 average rating, 241 reviews

A true Vermont get-away cabin in the woods

Badger Cottage offers a true rustic Vermont experience nestled in the woods with spectacular views and a quiet and peaceful ambiance. Once a barn, carefully reconstructed on the owners’ property, and modernized to today’s standards, this post and beam cabin is warm and cosy in winter and cool in summer. Well behaved dogs are very welcome and will enjoy the walks in the woods. Covid vaccinations are required. The owners live in an adjacent house with their very friendly Border Terrier

Guest favorite

A private mountain home is nestled among lush greenery, featuring a wooden exterior and a metal roof. The structure is complemented by a welcoming porch and surrounded by a neatly maintained lawn, creating a serene atmosphere against the forest backdrop.

Home in Middlesex

4.94 out of 5 average rating, 187 reviews

True Mountain House

This is a very private mountain home surrounded by green and peace. Your private forest. Amazing Views. Very romantic. Open layout. Lots of light. Wood floors and electric heating. Very quiet, relaxing and cozy. It has a decompressing effect on it's guests. Perfect to rest your head. Not suitable for children under 12 years old. Amazing gourmet kitchen. WE HAVE HIGH SPEED INTERNET. Fly into Burlington and rent a car, it will be approximately a 40min. Drive to Middlesex.

Guest favorite

The entrance features a white door with a glass panel, surrounded by soft green siding. A decorative white planter box holds flowers beneath the window. A wooden overhang provides shelter at the entryway, enhancing the welcoming appearance of the space.

Guesthouse in Montpelier

4.9 out of 5 average rating, 467 reviews

La Casita del Norte

La Casita del Norte is a private, bright, self-contained apartment in a small building separate from our home – a relaxing retreat in a quiet neighborhood within easy walking distance of Vermont College of Fine Arts, the State House and downtown Montpeler. WE ARE FOLLOWING AIRBNB’S NEW ENHANCED CLEANING AND SANITIZING PROTOCOL IN ORDER TO MAKE YOUR STAY AS SAFE AND WORRY-FREE AS POSSIBLE. And we use green cleaning products wherever possible.

Guest favorite

An open living space features a cozy seating area with a modern sectional sofa and a sleek coffee table. Natural light illuminates the room, with decorative plants and artwork enhancing the ambiance. The kitchen area showcases contemporary cabinetry and appliances, accompanied by exposed brick accents and a tin ceiling.

Apartment in Montpelier

4.96 out of 5 average rating, 395 reviews

Miles Court Downtown Montpelier

Curious about what makes the Smallest State Capital so amazing? Come stay at Miles Court named after Anne G. Miles in the 1890's. This is a newly renovated space combining late 19th century charm with modern conveniences. Right in downtown Montpelier there's no need to drive to enjoy the multiple restaurants and entertainment. Plus we're 30 minutes from all the skiing. Were centrally located in the heart of Vermont.

Vacation rentals for every style

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Popular amenities for Middlesex vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Middlesex

Guest favorite

A wooden bridge leads to the entrance of the treehouse, surrounded by trees displaying autumn colors. The structure features large windows and a unique architectural design, blending nature with handcrafted elements.

Treehouse in Waterbury

4.89 out of 5 average rating, 90 reviews

The Roost - Recharge & Relax

Guest favorite

An aerial view captures a secluded home surrounded by vibrant autumn foliage. The cozy structure with a green roof is set amidst an array of trees displaying rich reds, oranges, and yellows, highlighting the beauty of the natural landscape.

Home in Middlesex

4.91 out of 5 average rating, 76 reviews

The Vermont Red Barn

Top guest favorite

A modern cabin is nestled among tall trees, elevated on stilts. Large windows offer a glimpse of the interior space, featuring a minimalist design. The surrounding greenery creates a natural setting, while the pathway leading to the cabin is lined with earth tones.

Cabin in Morristown

5 out of 5 average rating, 200 reviews

Cady’s Falls Cabin

Top guest favorite

The exterior of a newly built hillside home is shown, featuring a wooden facade with a sloped roof. Surrounded by tall trees, the structure includes large windows and a garage attached to the side. A clear pathway leads to the entrance amidst a snowy landscape.

Home in Waterbury Village Historic District

4.99 out of 5 average rating, 71 reviews

Perry Pond House

Guest favorite

A vibrant red structure stands against a backdrop of rolling green hills and a clear blue sky. The sloped roof is metallic, reflecting the natural light. Surrounding vegetation, with hints of wildflowers, complements the scenic landscape of trees and distant mountains.

Guest suite in Montpelier

4.92 out of 5 average rating, 75 reviews

Farmhouse Sunset Studio at Anderbell Acres

Guest favorite

A cozy outdoor seating area is featured with two green adirondack chairs arranged around a round black table. The a-frame structure stands nearby, showcasing a transparent exterior that allows natural light to filter through. Lush greenery surrounds the setting, providing a serene atmosphere.

Tiny home in Middlesex

4.91 out of 5 average rating, 11 reviews

A-Frame Glamping

Top guest favorite

Guesthouse in Montpelier

5 out of 5 average rating, 71 reviews

Treetop Retreat

Guest favorite

An open living area features wooden walls and a light wood floor. A small kitchenette is visible with seating at a bar. A table with two patterned chairs is positioned next to a doorway, leading to the stairs. Natural light enters through a nearby window.

Apartment in Montpelier

4.91 out of 5 average rating, 53 reviews

Travelers Oasis in Montpelier

Quick stats about vacation rentals in Middlesex

Total rentals
150 properties
Nightly prices starting at
G$8,369 GYD before taxes and fees
Total number of reviews
12K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace

Frequently Asked Questions

Are there pet-friendly vacation rentals in Middlesex?
Four-legged friends are welcome in Middlesex. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Middlesex?
Experience the best of Middlesex with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Middlesex have free parking?
Absolutely! We offer over 70 house rentals with free parking in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Middlesex have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Middlesex. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Middlesex?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with wifi, over 20 homes with air conditioning, over 30 homes with a kitchen, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Middlesex have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Middlesex have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Middlesex. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Middlesex?
Yes! Work meets play with ease at over 60 vacation rentals in Middlesex featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Middlesex

Top-rated vacation rentals in Middlesex

Vacation rentals for every style

Popular amenities for Middlesex vacation rentals

Other great vacation rentals in Middlesex

Quick stats about vacation rentals in Middlesex

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore