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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Guest favourite

Barn in Middlesex

4.83 out of 5 average rating, 259 reviews

Four Season Country Escape at Lone Elm Farm

This 2nd floor barn apartment is a bright and airy space to enjoy quiet, cozy and private country living. Lone Elm Farm is an easy 5 mile drive from downtown Montpelier, 37 minutes to Stowe, VT and 1 hr 22 min. to the Canadian border. Many nordic and alpine ski resorts within an hours drive. Come experience sunrises and sunsets, Fall foliage, and snow (seasonal). The property is 40 acres of organic farm and forest and 1086 ft above the sea! We have adopted Airbnb's strict cleaning protocol

May 7 – 14

$150 CAD per night

Guest favourite

Barn in Middlesex

4.99 out of 5 average rating, 200 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.

Sep. 16 – 23

$201 CAD per night

Guest favourite

Guest suite in Middlesex

5.0 out of 5 average rating, 275 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.

Oct. 28 – Nov. 4

$192 CAD per night

Guest favourite

Guest suite in East Montpelier

4.94 out of 5 average rating, 269 reviews

Cottage Farmhouse Apartment in Heart of Vermont!

A sweet, bright, spacious, private second floor cottage-apartment in our 1830's brick farmhouse, close to Montpelier the bustling state capital, completely redecorated for guests with a comfortable queen bed in the sleeping area, vintage farmhouse kitchen and lovely living/dining room. Refinished maple floors and travertine tiled bathroom with a rain shower. Nestled into the countryside with eastern mountain views & active farm fields -glorious morning sun and black-out shades for sleeping in.

Jan. 18 – 25

$210 CAD per night

Guest favourite

Apartment in Waterbury

4.97 out of 5 average rating, 375 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.

Feb. 3 – 10

$150 CAD per night

Guest favourite

Cabin in Worcester

4.97 out of 5 average rating, 168 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

Feb. 24 – Mar. 3

$246 CAD per night

Guest favourite

Home in Waterbury Center

4.97 out of 5 average rating, 154 reviews

Vermont Getaway Home - Perfect Location

Central Location! Covered patio with propane fire table. Cozy 2 bed, 1.5 bath home, in a 2 unit duplex, approx 1200 sq.ft. Fully furnished. Whether you choose to stay in or want to get out, this is a great location! 13 mi. to Stowe Mtn., 21 to Sugarbush, 25 to Burlington, 3 to local hiking trails, and 4 to downtown Waterbury, enjoy local restaurants, craft beer, and more! Bedrooms and full bath are on 2nd floor and have window AC in summer months. Smoke Free, Pet Free Rental.

May 4 – 11

$257 CAD per night

Guest favourite

Home in Middlesex

4.93 out of 5 average rating, 155 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 internet. Fly into Burlington and rent a car, it will be approximately a 40min. Drive to Middlesex.

May 26 – Jun. 2

$288 CAD per night

Guest favourite

Guesthouse in Montpelier

4.89 out of 5 average rating, 382 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.

Jun. 10 – 17

$140 CAD per night

Guest favourite

Guest suite in Waterbury Center

4.94 out of 5 average rating, 415 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.

Apr. 18 – 25

$81 CAD per night

Guest favourite

Guest suite in Waterbury Center

4.86 out of 5 average rating, 126 reviews

Cozy Mountain Retreat with a View of Mt Hunger

Nestled in the heart of Vermont's best skiing, hiking and dining right between Waterbury and Stowe. We're just minutes to downtown yet the private driveway that opens to 10 acres feels like you're a world away. The apartment has a private locking entrance through a shared garage, well stocked kitchen, cozy sitting area with a view of the mountains and a full bathroom. The Queen bed wakes up to a fabulous view of Mt. Hunger.

May 8 – 15

$172 CAD per night

Guest favourite

Home in Montpelier

4.97 out of 5 average rating, 290 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.

Oct. 15 – 22

$156 CAD per night