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Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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

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Barn in Middlesex

4.97 out of 5 average rating, 221 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.

Guest suite in Middlesex

4.98 out of 5 average rating, 305 reviews

Morningstar Meadow - your home in Vermont

You have a home in Vermont! 5-star one-bedroom apartment has country charm and contemporary panache. A perfect retreat to enjoy rural serenity, stunning views, woods and fields. Everything you need: well-appointed with attractive, high quality furnishings, separate entrance, full kitchen, open living/dining area, cozy bedroom with queen bed. Cable TV, WiFi, and cell service. Plentiful free parking. Centrally located 3 miles from Montpelier. Snow tires or all-wheel drive recommended Nov-March.

Loft in Duxbury

4.98 out of 5 average rating, 117 reviews

Cozy Studio/Romantic Getaway

Take it easy at this cozy studio which is nestled in the hills of the beautiful Duxbury Vermont. Offered year round so that our guests can enjoy all that Vermont has to offer such as nearby skiing, changing leaves, hiking and so much more! Guests will enjoy their own private space with access to many amenities such as a full kitchen, private entrance, a queen bed, free WIFI and so much more! So grab a mug and sit back and relax next to the gas fireplace! You will want to return every season!

Rental unit in Waterbury

4.97 out of 5 average rating, 397 reviews

Village Oasis 2 -the crossroads of VT

A friend once referred to our town as Mayberry. It's definitely a small town where people look out for each other. In the heart of the village, walking distance from local restaurants, brewery's, and shops as well as mountain bike trails. 5 mi from a beach where you can rent canoes/kayaks/paddle boards. Enjoy the slopes, hiking, Ben and Jerry's, local brewery's, or the Vt. landscape, settle in with a warm jacuzzi tub. At the end of the day cozy up on a king sized bed watching Netflix's.

Cabin in Worcester

4.97 out of 5 average rating, 204 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 kambal yoga session for you and your companion. ☺️ Kambal sessions include sound healing, yoga nidra, energy work & weighted blankets for deep relaxation. -On site Minister Brook access--5 min. walk -Lots of skiing, hiking, water to explore -18 min to Montpelier- funky downtown, eccentric shops & restaurants

Rental unit in Montpelier

4.89 out of 5 average rating, 145 reviews

The Studio - in the heart of Montpelier

Welcome to The Studio in downtown Montpelier. This second floor unit is a cozy one bedroom with all you need for your stay. This charming renovated historic building is now an eclectic artful space with a separate bedroom, living room and kitchen/dining area. Walk to everything from here! One block to city center and all the downtown restaurants and shops. Parking is street parking and there are municipal lots as well. The perfect central location for exploring the surrounding areas.

Home in Middlesex

4.94 out of 5 average rating, 173 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 suite in Waterbury Center

4.95 out of 5 average rating, 244 reviews

Modern Farmhouse with Sunset Mountain Views

Sunny, bright and private space, cheerfully decorated, with the comfiest beds and coziest linens. Located a world away from peak season crowds but everything is nearby, only one mile off Rt 100. Minutes from the best skiing, bike trails, kayaking, and hiking in the east. 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!l

Guesthouse in Montpelier

4.89 out of 5 average rating, 433 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 suite in Waterbury Center

4.94 out of 5 average rating, 444 reviews

Waterbury Center Guest Bedroom - 244 Howard

The guestroom room is very cozy with radiant heat in the floor during the winter. The separate entrance is off a covered porch. The porch has chairs and a table and is very pleasant in the warmer months The little kitchen alcove is convenient for coffee or tea or a light meal. We live in a historic building and our neighborhood is located very close to Rte 100. Waterbury village and Stowe as well as skiing, hiking and biking are all nearby.

Home in Montpelier

4.97 out of 5 average rating, 313 reviews

Cozy, sunny apt. in Montpelier, Vt.

Bright, quiet, second floor one bedroom apt. in 150 yr. old home. View of garden, king size bed, full kitchen, and large bathroom . Shared entrance into the house, private entrance into the apartment, one off street parking space and a safe 5 to 7 minute walk to our vibrant downtown. Must be able to negotiate stairs as the apartment is on the second floor. 2 night minimum stay and 10 day maximum stay No pets please.

Cabin in Waterbury Center

4.97 out of 5 average rating, 182 reviews

44 Degrees North

This cozy 3 bed 2 bath cabin is situated on the southern end of the Worcester Range in Waterbury Center. Enjoy beautiful sunsets over Camel's Hump and Bolton Mnt while sipping cocktails on the deck. Or warm up in the in the hot tub during the winter while watching the cats groom the trails at Stowe . Hike, bike and snowmobile from your doorstep or treat yourself to VT craft beers and eats just a short 5-7min drive away.

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Popular amenities for Middlesex vacation rentals

Free parking on premises

Air conditioning

Stay near Middlesex's top sights

Cold Hollow Cider Mill146 locals recommend

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

Other great vacation rentals in Middlesex

Home in Waterbury Center

4.98 out of 5 average rating, 110 reviews

Cozy Farmhouse Nestled Between Stowe and Waterbury

Rental unit in Montpelier

4.81 out of 5 average rating, 98 reviews

Cozy Capital Stay

Rental unit in Waterbury

4.93 out of 5 average rating, 194 reviews

1880 Purple Village Victorian

Home in Waterbury Center

4.97 out of 5 average rating, 185 reviews

Vermont Getaway Home - Perfect Location

Guesthouse in Williamstown

4.98 out of 5 average rating, 135 reviews

The Tiny Home with Barrel Sauna

Guesthouse in Montpelier

5 out of 5 average rating, 40 reviews

Treetop Retreat

Rental unit in Waterbury

4.91 out of 5 average rating, 335 reviews

Waterbury Village Townhouse

Home in Moretown

4.97 out of 5 average rating, 147 reviews

Lovely Waterbury Home (Crossroads of Recreation)

Quick stats about vacation rentals in Middlesex

Total rentals
140 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
12K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
70 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 30 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Middlesex?
Experience the best of Middlesex with our house rentals, starting at about $60 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 house rentals in Middlesex have a kitchen?
Absolutely! We offer over 60 house 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 20 homes with air conditioning, over 30 homes with free parking, over 30 homes with wifi, over 30 homes with a kitchen, 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 house rentals in Middlesex have wifi?
Absolutely! We offer over 70 house 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 70 vacation rentals in Middlesex featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore