Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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Guest favorite

Apartment in Waterbury

4.98 out of 5 average rating, 318 reviews

Village Suite

Modern + charming apartment with private entrance + deck located in Historic Waterbury Village within walking distance to popular shopping, coffee shops, pubs, and restaurants. The building is also home to the Stowe Street Cafe and Bridgeside Bookstore with plenty more shops and eateries just a short walk away. Bolton Valley, Sugarbush, and Stowe Mountain Resorts are just a 20-30 minute drive, and the Ben & Jerry's Factory and Waterbury Reservoir are less than 10 miles north. A perfect location!

Guest favorite

Barn in Middlesex

4.99 out of 5 average rating, 201 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 favorite

Guest suite in Middlesex

5.0 out of 5 average rating, 277 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.

Guest favorite

Bungalow in Worcester

4.97 out of 5 average rating, 588 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!

Guest favorite

Cabin in Worcester

4.97 out of 5 average rating, 174 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

Guest favorite

Apartment in Waterbury

4.97 out of 5 average rating, 379 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.

Guest favorite

Home in Waterbury Center

4.97 out of 5 average rating, 155 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.

Guest favorite

Home in Middlesex

4.93 out of 5 average rating, 156 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.

Guest favorite

Guesthouse in Montpelier

4.89 out of 5 average rating, 387 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

Guest suite in Waterbury Center

4.94 out of 5 average rating, 418 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.

Guest favorite

Home in Montpelier

4.97 out of 5 average rating, 292 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.

Guest favorite

Guest suite in Waterbury Center

4.96 out of 5 average rating, 220 reviews

Modern Farmhouse with Sunset Mountain Views

Spectacular, expansive views from Mt Mansfield to Camel's Hump! Watch the sunset from adirondack chairs right outside your door. Sunny, bright and private space. A world away but everything nearby, one mile off Rt 100. Minutes from the best skiing, bike trails, kayaking, and hiking in the east. 10 min to Stowe, 18 to lifts, 30 Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middlesex vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Middlesex's top sights

Three Penny Taproom102 locals recommend

The Skinny Pancake46 locals recommend

Positive Pie76 locals recommend

J Morgan's Steakhouse18 locals recommend

Red Hen Baking46 locals recommend

Mad Taco25 locals recommend

Other great vacation rentals in Middlesex

Guest favorite

Guest suite in East Montpelier

4.94 out of 5 average rating, 270 reviews

Cottage Farmhouse Apartment in Heart of Vermont!

Guest favorite

Farm stay in Berlin

4.95 out of 5 average rating, 177 reviews

Farm Stay - Working livestock farm

Guest favorite

Apartment in Montpelier

4.87 out of 5 average rating, 607 reviews

Entire 2nd Floor Walk to Montpelier

Guest favorite

Guest suite in Waterbury Center

4.86 out of 5 average rating, 127 reviews

Cozy Mountain Retreat with a View of Mt Hunger

Guest favorite

Home in Waterbury Center

4.98 out of 5 average rating, 134 reviews

Vermont vacation house

Guest favorite

Apartment in Montpelier

4.89 out of 5 average rating, 112 reviews

The Studio - in the heart of Montpelier

Guest favorite

Yurt in Montpelier

4.95 out of 5 average rating, 512 reviews

Private 4-Season Country Yurt Close to Town

Guest favorite

Guest suite in Moretown

4.96 out of 5 average rating, 111 reviews

The Nest Studio

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Quick stats about vacation rentals in Middlesex

Total rentals
150 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
11K reviews
Nightly prices starting at
$40 before taxes and fees

Frequently Asked Questions

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.
Are there family-friendly vacation rentals in Middlesex?
Middlesex has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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.
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 80 house rentals with wifi in Middlesex. Enjoy a tailored experience with all the comforts you desire.
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 apartment rentals in Middlesex have free parking?
Absolutely! We offer over 20 apartment 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.

Vacation rentals in Middlesex

Top-rated vacation rentals in Middlesex

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Middlesex vacation rentals

Stay near Middlesex's top sights

Other great vacation rentals in Middlesex

Guest suite in East Montpelier

Farm stay in Berlin

Apartment in Montpelier

Guest suite in Waterbury Center

Home in Waterbury Center

Apartment in Montpelier

Yurt in Montpelier

Guest suite in Moretown

Quick stats about vacation rentals in Middlesex

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Middlesex?

Are there family-friendly vacation rentals in Middlesex?

Are there pet-friendly vacation rentals in Middlesex?

Do apartment rentals in Middlesex have air conditioning?

Do house rentals in Middlesex have wifi?

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

Do apartment rentals in Middlesex have free parking?

Do apartment rentals in Middlesex have a kitchen?

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