Vacation rentals in Middlebury

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middlebury

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

Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 265 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Apr 4 – 11

G$32,436 GYD per night
Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 162 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Aug 17 – 24

G$15,054 GYD per night
Guest favorite

Home in Woodbury

4.99 out of 5 average rating, 110 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this sanitized, rambling, relaxing, light-filled 2 story 4 bedroom 2.5 bath on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from 5 popular, fabulous restaurants. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."

Nov 24 – Dec 1

G$67,493 GYD per night

Popular amenities for Middlebury vacation rentals

Stay near Middlebury's top sights

Maggie McFly's® Middlebury3 locals recommend
Spartan3 locals recommend
Vyne Restaurant & Bar4 locals recommend
Pies & Pints of Middlebury3 locals recommend
Ocean State Job Lot3 locals recommend
Hop Brook Lake10 locals recommend

Other great vacation rentals in Middlebury

Guest favorite

Home in Waterbury

4.9 out of 5 average rating, 31 reviews

Come and enjoy the BURY's of CT!

May 31 – Jun 7

G$39,169 GYD per night
Superhost

Home in Watertown

4.89 out of 5 average rating, 36 reviews

Tiny Home Away From Home - Complete Privacy, Peace

Apr 29 – May 6

G$27,497 GYD per night
Guest favorite

Apartment in Southbury

4.87 out of 5 average rating, 87 reviews

Suite Hill studio

Sep 12 – 19

G$29,405 GYD per night
Guest favorite

Guest suite in Waterbury

4.9 out of 5 average rating, 63 reviews

Private cozy getaway

Aug 10 – 17

G$26,648 GYD per night
Guest favorite

Guest suite in Waterbury

4.96 out of 5 average rating, 95 reviews

The Executive LLC

Jun 1 – 8

G$29,921 GYD per night
Guest favorite

Guest suite in Wolcott

5.0 out of 5 average rating, 13 reviews

Modern cozy, pet friendly

Jun 5 – 12

G$30,554 GYD per night
Guest favorite

Home in Southbury

5.0 out of 5 average rating, 53 reviews

The Cottage at Cedar Spring Farm

May 31 – Jun 7

G$33,673 GYD per night
Guest favorite

Loft in Woodbury

5.0 out of 5 average rating, 30 reviews

Country Loft

Nov 28 – Dec 5

G$30,575 GYD per night
Guest favorite

Guest suite in Plymouth

5.0 out of 5 average rating, 20 reviews

Secluded | Cozy | Nature

Jul 4 – 11

G$20,626 GYD per night
Guest favorite

Home in Waterbury

4.95 out of 5 average rating, 57 reviews

Amazing views of the Brass City

Jan 28 – Feb 4

G$30,419 GYD per night
Guest favorite

Apartment in Bethlehem

5.0 out of 5 average rating, 77 reviews

C&C Rush Haven Farm, A Sanctuary for All Life!

Oct 28 – Nov 4

G$29,670 GYD per night
Guest favorite

Home in Southington

4.95 out of 5 average rating, 62 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

Aug 26 – Sep 2

G$87,584 GYD per night

Quick stats about vacation rentals in Middlebury

Total rentals

30 properties

Popular amenities

Gym, BBQ grill, and Laptop-friendly workspace

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Total number of reviews

1K reviews

Frequently Asked Questions

  • Do house rentals in Middlebury have wireless internet?

    Absolutely! We offer over 20 house rentals with wireless internet in Middlebury. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Middlebury?

    Four-legged friends are welcome in Middlebury. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Middlebury have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Middlebury. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Middlebury?

    Make yourself at home in Middlebury by choosing from our most frequently booked neighborhoods. We have over 120 vacation rentals in Hop Brook, and over 100 vacation rentals in Bunker Hill.

  • Are there vacation rentals with a dedicated workspace in Middlebury?

    Yes! Work meets play with ease at over 10 vacation rentals in Middlebury featuring dedicated workspaces. Stay connected and productive in your home away from home.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore