Holiday rentals in Middlebury
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Top-rated holiday rentals in Middlebury
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest house 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).
4–11 Apr
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!
17–24 Aug
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."
24 Nov – 1 Dec
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlebury holiday rentals
Other great holiday rentals in Middlebury
Home in Waterbury
4.9 out of 5 average rating, 31 reviewsCome and enjoy the BURY's of CT!
31 May – 7 Jun
Home in Watertown
4.89 out of 5 average rating, 36 reviewsTiny Home Away From Home - Complete Privacy, Peace
29 Apr – 6 May
Flat in Southbury
4.87 out of 5 average rating, 87 reviewsSuite Hill studio
12–19 Sept
Guest suite in Waterbury
4.9 out of 5 average rating, 63 reviewsPrivate cozy getaway
10–17 Aug
Guest suite in Waterbury
4.96 out of 5 average rating, 95 reviewsThe Executive LLC
1–8 Jun
Guest suite in Wolcott
5.0 out of 5 average rating, 13 reviewsModern cozy, pet friendly
5–12 Jun
Home in Southbury
5.0 out of 5 average rating, 53 reviewsThe Cottage at Cedar Spring Farm
31 May – 7 Jun
Loft in Woodbury
5.0 out of 5 average rating, 30 reviewsCountry Loft
28 Nov – 5 Dec
Guest suite in Plymouth
5.0 out of 5 average rating, 20 reviewsSecluded | Cozy | Nature
4–11 Jul
Home in Waterbury
4.95 out of 5 average rating, 57 reviewsAmazing views of the Brass City
28 Jan – 4 Feb
Flat in Bethlehem
5.0 out of 5 average rating, 77 reviewsC&C Rush Haven Farm, A Sanctuary for All Life!
28 Oct – 4 Nov
Home in Southington
4.95 out of 5 average rating, 62 reviewsConnecticut Chalet - Private Pond, Firepit, Views!
26 Aug – 2 Sept
Quick stats about holiday 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 |
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