Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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Guest favorite

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

R1,762 ZAR per night

Guest favorite

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.

Aug 10 – 17

R2,535 ZAR per night

Guest favorite

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.

Nov 1 – 8

R2,399 ZAR per night

Guest favorite

Guest suite in Waterbury Center

4.98 out of 5 average rating, 120 reviews

Brand New Cozy Mountain Guest Suite in Waterbury

Cozy, private, spacious mountain studio above our garage in historic Waterbury Center. Full kitchen and full bathroom, quiet private deck with mountain views to watch the sunrise each morning. The unit is tucked away under the Worcester Mountains so you can enjoy a comfortable, quiet Vermont experience. Hiking and mountain biking trails are 5-10 minutes away. Stowe is 15 minutes and Waitsfield is 20 minutes away, easy access to I-89 and a 35 minute drive to Burlington to visit Lake Champlain

May 2 – 9

R2,699 ZAR per night

Guest favorite

Apartment in Waterbury

4.97 out of 5 average rating, 376 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.

Dec 9 – 16

R1,785 ZAR per night

Guest favorite

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

Jan 13 – 20

R2,958 ZAR per night

Guest favorite

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.

Jun 5 – 12

R3,102 ZAR per night

Guest favorite

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 4 – 11

R3,401 ZAR per night

Guest favorite

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.

Jul 5 – 12

R1,676 ZAR per night

Guest favorite

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.

Nov 2 – 9

R1,044 ZAR per night

Guest favorite

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 24 – 31

R1,914 ZAR per night

Guest favorite

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

R1,881 ZAR per night

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

Apartment in Waterbury

4.95 out of 5 average rating, 180 reviews

1880 Purple Village Victorian

Dec 5 – 12

R2,780 ZAR per night

Guest favorite

Guest suite in East Montpelier

4.94 out of 5 average rating, 269 reviews

Cottage Farmhouse Apartment in Heart of Vermont!

Dec 29 – Jan 5

R2,574 ZAR per night

Guest favorite

Apartment in Montpelier

4.89 out of 5 average rating, 112 reviews

The Studio - in the heart of Montpelier

Feb 22 – Mar 1

R1,896 ZAR per night

Guest favorite

Yurt in Montpelier

4.95 out of 5 average rating, 508 reviews

Private 4-Season Country Yurt Close to Town

Dec 8 – 15

R2,076 ZAR per night

Guest favorite

Casa particular in Waterbury Village Historic District

4.93 out of 5 average rating, 103 reviews

Private First Floor Room with Patio and Sauna

Jun 26 – Jul 3

R1,738 ZAR per night

Guest favorite

Apartment in Waterbury

4.98 out of 5 average rating, 317 reviews

Village Suite

Nov 15 – 22

R3,048 ZAR per night

Guest favorite

Guest suite in Waterbury Center

4.96 out of 5 average rating, 219 reviews

Modern Farmhouse with Sunset Mountain Views

Dec 2 – 9

R3,444 ZAR per night

Guest favorite

Home in Middlesex

5.0 out of 5 average rating, 18 reviews

Pet friendly, sunset & mountain view VT retreat

May 31 – Jun 7

R1,945 ZAR per night

Show all

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
R769 ZAR before taxes and fees

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 80 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 70 house rentals with a kitchen in Middlesex. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Middlesex?
Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with free parking, over 40 homes with air conditioning, over 70 homes with a kitchen, over 80 homes with wifi, 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 70 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

Apartments

Houses

Hotels

Popular amenities for Middlesex vacation rentals

Stay near Middlesex's top sights

Other great vacation rentals in Middlesex

Apartment in Waterbury

Guest suite in East Montpelier

Apartment in Montpelier

Yurt in Montpelier

Casa particular in Waterbury Village Historic District

Apartment in Waterbury

Guest suite in Waterbury Center

Home in Middlesex

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 pet-friendly vacation rentals in Middlesex?

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

Do house rentals in Middlesex have free parking?

Do house rentals in Middlesex have a kitchen?

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

Do apartment rentals in Middlesex have air conditioning?

Do apartment rentals in Middlesex have wifi?

Are there vacation rentals with a dedicated workspace in Middlesex?

Destinations to explore