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.
Guesthouse in Southbury
4.93 out of 5 average rating, 265 reviewsCharming 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
Guest suite in Watertown
4.91 out of 5 average rating, 162 reviewsLrg 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
Home in Woodbury
4.99 out of 5 average rating, 110 reviewsYour 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlebury vacation rentals
Other great vacation rentals in Middlebury
Home in Waterbury
4.9 out of 5 average rating, 31 reviewsCome and enjoy the BURY's of CT!
May 31 – Jun 7
Home in Watertown
4.89 out of 5 average rating, 36 reviewsTiny Home Away From Home - Complete Privacy, Peace
Apr 29 – May 6
Apartment in Southbury
4.87 out of 5 average rating, 87 reviewsSuite Hill studio
Sep 12 – 19
Guest suite in Waterbury
4.9 out of 5 average rating, 63 reviewsPrivate cozy getaway
Aug 10 – 17
Guest suite in Waterbury
4.96 out of 5 average rating, 95 reviewsThe Executive LLC
Jun 1 – 8
Guest suite in Wolcott
5.0 out of 5 average rating, 13 reviewsModern cozy, pet friendly
Jun 5 – 12
Home in Southbury
5.0 out of 5 average rating, 53 reviewsThe Cottage at Cedar Spring Farm
May 31 – Jun 7
Loft in Woodbury
5.0 out of 5 average rating, 30 reviewsCountry Loft
Nov 28 – Dec 5
Guest suite in Plymouth
5.0 out of 5 average rating, 20 reviewsSecluded | Cozy | Nature
Jul 4 – 11
Home in Waterbury
4.95 out of 5 average rating, 57 reviewsAmazing views of the Brass City
Jan 28 – Feb 4
Apartment in Bethlehem
5.0 out of 5 average rating, 77 reviewsC&C Rush Haven Farm, A Sanctuary for All Life!
Oct 28 – Nov 4
Home in Southington
4.95 out of 5 average rating, 62 reviewsConnecticut Chalet - Private Pond, Firepit, Views!
Aug 26 – Sep 2
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.
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