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Vacation rentals in Middlesex

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Popular amenities for Middlesex vacation rentals

Other great vacation rentals in Middlesex

Guest favorite
A naturally finished wooden interior is presented with panoramic windows offering views of the surrounding trees. A central dining table is surrounded by cozy seating with cushions, while a soft armchair complements the space. This arrangement encourages relaxation and connection with nature.
Treehouse in Waterbury
4.93 out of 5 average rating, 58 reviews

The Roost - Recharge & Relax

KevinRating, 5 stars2 weeks ago
Amazing place. Right off the road but feels very private. It really was like sleeping in the trees. Sandra is a super helpful and friendly host. The house was comfortable and clean, but it still felt like an adventure! My son and I had a blast:)
Top guest favorite
A spacious deck is shown with wooden flooring, partially covered in snow. The railing offers an unobstructed view of a pond and trees, with a sunset casting warm colors across the sky. Sliding glass doors lead into the home, enhancing the indoor-outdoor connection.
Home in Waterbury Village Historic District
4.98 out of 5 average rating, 62 reviews

Perry Pond House

KirillRating, 5 stars3 months ago
Great place. Nice location.
Superhost
Cottage in Calais
4.98 out of 5 average rating, 92 reviews

Cozy Peaceful Cottage

AdrienneRating, 5 stars7 months ago
Morgan is the perfect host, providing everything necessary to a magical stay in their remarkable cabin. I had complete privacy and quiet, but knew she was readily available if I had any questions or needs. The cabin itself is a wonder of architecture, with every detail carefully thought out and rendered. There are books galore and CDs, the slipper foot bathtub is amazing, and the back patio offers a peaceful view of trees and meadow. The property is dotted with wonderful sculptures by her husband, Alan. I watched the sun rise and set and walked down the very dark night road to look at the stars. The woods are my favorite place to be, and there was no shortage of local hiking trails. The general store just down the street is staffed by very friendly folks, and I bought a new favorite coffee mug made by a local artisan. In short, my stay was everything I hoped it would be, and I would highly recommend it.
Superhost
A cozy living area features a modern gray sofa complemented by a wooden coffee table. A soft rug covers the floor, while large windows allow natural light to illuminate the space, providing views of the surrounding trees and outdoor area.
Guesthouse in Plainfield
4.87 out of 5 average rating, 60 reviews

Cozy 1 bed guest suite Sugarwood home

TeresaRating, 5 stars2 weeks ago
The place was delightful—a very cute getaway without being completely remote. The space was perfect for two people. It had everything you needed, and it was very cozy and spacious. I highly recommend it. Jungwood was extremely communicative and helpful during the stay.
Guest favorite
A close-up view of a pale yellow flower in the foreground, surrounded by green foliage. In the background, a red barn can be seen against a landscape of rolling hills and mountains under a clear blue sky.
Guest suite in Montpelier
4.92 out of 5 average rating, 74 reviews

Farmhouse Sunset Studio at Anderbell Acres

WilsonRating, 5 stars4 months ago
My partner and I had a great time at the guest suite. We hope to stay again in the future.
Top guest favorite
A serene waterfall cascades over rocky terrain, surrounded by vibrant greenery. The water flows into a tranquil pool, reflecting the natural landscape. In the background, a wooden bridge connects the area to a cozy post and beam house nestled among the trees.
Home in Waterbury Village Historic District
4.94 out of 5 average rating, 36 reviews

Waterfall Oasis with Large Deck

BethRating, 5 stars2 days ago
If you have the opportunity to stay at this amazing home, do it. The bridge leads you to a private and beautiful home that is exactly what you would expect from the pictures. The hosts are friendly, responsive and helpful. The home was the best stocked Airbnb I have ever stayed at. So welcoming and so many thoughtful touches. We used the grill to cook dinner on the deck overlooking the waterfall, watched fireflies in the field in the evening and enjoyed coffee from the living room every morning. We also going Waterbury to be a perfect location for exploring Vermont.
Top guest favorite
A scenic view of rolling mountains is framed by trees adorned with autumn foliage. The landscape showcases a mix of vibrant reds, oranges, and greens, under a sky dotted with fluffy clouds that enhance the natural beauty of the Vermont countryside.
Apartment in Waterbury
5 out of 5 average rating, 20 reviews

"Stowebury" Apartment

TiffanyRating, 5 stars2 weeks ago
Dan’s place was even better than we expected.! You could tell a lot of thought was put into making the space very comfortable with added touches to make you feel at home. While the space is smaller, it has everything that you would need. We were bummed that it rained on the evening that we planned to use the fire pit but it looked like a nice evening spot to relax. I would highly recommend to others!
Superhost
Apartment in Montpelier
4.97 out of 5 average rating, 71 reviews

Stylish Montpelier 2BR Apt. Walk to town

JenniferRating, 5 stars63 months ago
Lucy is a welcoming and helpful host. The apartment was just perfect; clean, comfortable, nicely decorated and the beds were exceptional! Lucy went the extra mile to have all of the necessary kitchen utensils and it was so to have a washer and dryer right in the apartment. The location was perfect with great walks right out the door.

Quick stats about vacation rentals in Middlesex

  • Total rentals

    150 properties

  • Nightly prices starting at

    G$8,366 GYD before taxes and fees

  • Total number of reviews

    13K reviews

  • Family-friendly rentals

    70 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

  • Do house rentals in Middlesex have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Middlesex. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Middlesex have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Middlesex. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • Do house rentals in Middlesex have self check-in?

    Absolutely! We offer over 20 house rentals with self check-in in Middlesex. Enjoy a tailored experience with all the comforts you desire.

  • 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.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with wifi, over 20 homes with self check-in, over 10 homes with a gym, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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 60 vacation rentals in Middlesex featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Washington County
  5. Middlesex