Holiday rentals in Middlebury

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middlebury

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

Guest favourite

Guest house 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).

4–11 Apr

£144 per night
Guest favourite

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!

17–24 Aug

£71 per night
Guest favourite

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."

24 Nov – 1 Dec

£312 per night

Popular amenities for Middlebury holiday 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 holiday rentals in Middlebury

Guest favourite

Home in Waterbury

4.9 out of 5 average rating, 31 reviews

Come and enjoy the BURY's of CT!

31 May – 7 Jun

£181 per night
Superhost

Home in Watertown

4.89 out of 5 average rating, 36 reviews

Tiny Home Away From Home - Complete Privacy, Peace

29 Apr – 6 May

£126 per night
Guest favourite

Flat in Southbury

4.87 out of 5 average rating, 87 reviews

Suite Hill studio

12–19 Sept

£133 per night
Guest favourite

Guest suite in Waterbury

4.9 out of 5 average rating, 63 reviews

Private cozy getaway

10–17 Aug

£122 per night
Guest favourite

Guest suite in Waterbury

4.96 out of 5 average rating, 95 reviews

The Executive LLC

1–8 Jun

£140 per night
Guest favourite

Guest suite in Wolcott

5.0 out of 5 average rating, 13 reviews

Modern cozy, pet friendly

5–12 Jun

£149 per night
Guest favourite

Home in Southbury

5.0 out of 5 average rating, 53 reviews

The Cottage at Cedar Spring Farm

31 May – 7 Jun

£151 per night
Guest favourite

Loft in Woodbury

5.0 out of 5 average rating, 30 reviews

Country Loft

28 Nov – 5 Dec

£151 per night
Guest favourite

Guest suite in Plymouth

5.0 out of 5 average rating, 20 reviews

Secluded | Cozy | Nature

4–11 Jul

£94 per night
Guest favourite

Home in Waterbury

4.95 out of 5 average rating, 57 reviews

Amazing views of the Brass City

28 Jan – 4 Feb

£148 per night
Guest favourite

Flat in Bethlehem

5.0 out of 5 average rating, 77 reviews

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

28 Oct – 4 Nov

£134 per night
Guest favourite

Home in Southington

4.95 out of 5 average rating, 62 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

26 Aug – 2 Sept

£401 per night

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

Destinations to explore