Holiday rentals in Woodbury

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Woodbury

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

₹12,908 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

₹5,991 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

₹26,858 per night

Popular amenities for Woodbury holiday rentals

Stay near Woodbury's top sights

Market Place Kitchen and Bar30 locals recommend
Max Prime Steakhouse9 locals recommend
New Morning Market29 locals recommend
Dottie's7 locals recommend
Good News Restaurant and Bar22 locals recommend
San Remo Restaurant-Pizzeria3 locals recommend

Other great holiday rentals in Woodbury

Guest favourite

Flat in Waterbury

4.98 out of 5 average rating, 64 reviews

Everything you need! Apartment!

14–21 Jan

₹9,285 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

₹10,942 per night
Guest favourite

Home in Woodbury

5.0 out of 5 average rating, 11 reviews

The Birches on Main - Ca 1753

28 May – 4 Jun

₹24,003 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

₹13,400 per night
Guest favourite

Holiday home in Woodbury

5.0 out of 5 average rating, 27 reviews

The Meadow Farmhouse

22–29 Apr

₹39,984 per night
Guest favourite

Cottage in Bethlehem

5.0 out of 5 average rating, 27 reviews

Cottage Getaway | Peaceful Setting | Pet Friendly

25 Oct – 1 Nov

₹20,572 per night
Guest favourite

Home in Woodbury

5.0 out of 5 average rating, 8 reviews

Beautiful Litchfield - 2 homes in one

29 May – 5 Jun

₹41,578 per night
Guest favourite

Home in Woodbury

4.97 out of 5 average rating, 36 reviews

Renovated Connecticut Country House sleeps 14!

2–9 Aug

₹43,303 per night
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

₹15,587 per night
Guest favourite

Flat in Southbury

4.87 out of 5 average rating, 87 reviews

Suite Hill studio

12–19 Sep

₹11,702 per night
Guest favourite

Guest suite in Washington

5.0 out of 5 average rating, 36 reviews

Custom industrial farmhouse Apt in Washington Dpt

13–20 Dec

₹12,064 per night
Guest favourite

Guest suite in Plymouth

5.0 out of 5 average rating, 20 reviews

Secluded | Cozy | Nature

4–11 Jul

₹8,208 per night

Quick stats about holiday rentals in Woodbury

Total rentals

30 properties

Wifi availability

30 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

850 reviews

Destinations to explore