Woodbury Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Woodbury holiday rentals

Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.6 out of 10, Exceptional, (10)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is HK$1,019
HK$2,431 total
includes taxes & fees
28 Dec - 29 Dec
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is HK$658
HK$1,271 total
includes taxes & fees
23 Dec - 24 Dec
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
1 bedroom, desk, iron/ironing board, WiFi
One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
10.0 out of 10, Exceptional, (2)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is HK$739
HK$1,603 total
includes taxes & fees
23 Dec - 24 Dec
One bedroom apartment in United States of America, New Haven
Private kitchen
Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking

Westville Stay • 2BR • Near Yale • Free Parking
West New Haven
10.0 out of 10, Exceptional, (3)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is HK$630
HK$1,829 total
includes taxes & fees
8 Jan - 9 Jan 2026
Westville Stay • 2BR • Near Yale • Free Parking
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury
Southbury
9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is HK$700
HK$961 total
includes taxes & fees
29 Dec - 30 Dec
New One Bedroom Apartment Centrally Located in Southbury
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
Downtown New Haven
9.0 out of 10, Wonderful, (12)
"Convenient location. Just off Rte 91. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. "
United States
Lois G.
The price is HK$521
HK$1,408 total
includes taxes & fees
29 Dec - 30 Dec
Charming Studio| Near Yale| Downtown New Haven
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Shelton
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is HK$934
HK$1,531 total
includes taxes & fees
23 Dec - 24 Dec
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Fridge, microwave, oven, stovetop
#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is HK$908
HK$1,822 total
includes taxes & fees
5 Jan - 6 Jan 2026
#26 Beautifully Renovated 2 BR Home
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.6 out of 10, Exceptional, (4)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is HK$693
HK$2,658 total
includes taxes & fees
30 Dec - 31 Dec
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
9.0 out of 10, Wonderful, (8)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is HK$693
HK$952 total
includes taxes & fees
3 Jan - 4 Jan 2026
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$895
HK$2,243 total
includes taxes & fees
2 Jan - 3 Jan 2026
Once the old Schools house now a newly furnished Apartment
Exterior
Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (69)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is HK$1,012
HK$1,766 total
includes taxes & fees
27 Dec - 28 Dec
Spacious 2 Bedroom apartment close to Yale Bowl
Interior
The Nest At Elm City Flats.

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.4 out of 10, Exceptional, (6)
"Nice place! Short but sweet trip. Appreciate how quick your communication was and your accommodations!"
United States
Lori K.
The price is HK$693
HK$1,819 total
includes taxes & fees
23 Dec - 24 Dec
The Nest At Elm City Flats.
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (7)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$895
HK$2,243 total
includes taxes & fees
27 Dec - 28 Dec
All New 1BR with tons of Charm
Interior
Private Apartment in Southbury 101

Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
The price is HK$825
HK$2,096 total
includes taxes & fees
19 Jan - 20 Jan 2026
Private Apartment in Southbury 101
Exterior
Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is HK$959
HK$2,471 total
includes taxes & fees
23 Dec - 24 Dec
Angelica’s safe haven @ west haven
Exterior
Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is HK$910
HK$2,991 total
includes taxes & fees
30 Dec - 31 Dec
Cozy Modern Farmhouse Private Apt - 3 Beds
Microwave, oven, stovetop, dishwasher
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.

Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
2.0 star property
Southbury
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$983
HK$1,599 total
includes taxes & fees
7 Jan - 8 Jan 2026
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
Exterior
Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is HK$895
HK$2,243 total
includes taxes & fees
3 Jan - 4 Jan 2026
Newly Remodeled with deck. Close to town center
Fridge, microwave, oven, stovetop
Yale Casa Verde Studio

Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.6 out of 10, Exceptional, (8)
"Had a great stay!"
United States
Jeffrey C.
The price is HK$739
HK$1,587 total
includes taxes & fees
23 Dec - 24 Dec
Yale Casa Verde Studio
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Woodbury Hotel Reviews

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"The room was spacious. The bar was nice."
Robert 1-night trip
Posted 2 days ago
Wyndham Southbury

Find out more about Woodbury

Search for holiday rentals in Woodbury on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodbury using one of the methods below:

  • View our selection of featured holiday rentals in Woodbury
  • Use the map to find apartments and other holiday homes in the Woodbury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodbury while they last

Look no further and take a look at our great range of rental properties in Woodbury!

Frequently asked questions

Are there holiday rentals in Woodbury?

Yes, there are holiday rentals in Woodbury close to Glebe House Museum and The Gertrude Jekyll Garden, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Woodbury has a good selection of restaurants. Make sure you have time to check out the ski areas and coffee shops during your trip.

What are some of the best holiday rentals that Woodbury has to offer?

Room-plaid Room 3min From Yale Univ: This holiday home rental outside Woodbury comes with free WiFi so that you can feel at home during your trip. Kitchen amenities such as a fridge and a microwave can make your holiday run smoothly.

How many holiday rentals are there in Woodbury?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Woodbury stay.

What can I see and do in Woodbury?

Hollow Park and Lake Quassapaug are a couple of scenic spots to enjoy the outdoors, whereas Glebe House Museum and The Gertrude Jekyll Garden is one of the cultural attractions. Other places in town to visit include Pilgrim Mall Shopping Center and Woodbury Ski Area.

What are holiday rentals like in Woodbury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodbury. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.