Woodbury Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Woodbury vacation rentals

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 ￥12,526
￥36,638 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Westville Stay • 2BR • Near Yale • Free Parking
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 ￥17,379
￥29,036 total
includes taxes & fees
Dec 30 - Dec 31
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
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.
Once the old Schools house now a newly furnished Apartment
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
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is ￥13,935
￥19,157 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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 ￥18,261
￥36,656 total
includes taxes & fees
Jan 5 - Jan 6, 2026
#26 Beautifully Renovated 2 BR Home
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, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is ￥13,387
￥18,527 total
includes taxes & fees
Dec 30 - Dec 31
New One Bedroom Apartment Centrally Located in Southbury
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 ￥13,387
￥25,729 total
includes taxes & fees
Dec 31 - Jan 1, 2026
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
9.4 out of 10, Exceptional, (3)
"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 ￥14,874
￥32,253 total
includes taxes & fees
Dec 30 - Dec 31
One bedroom apartment in United States of America, New Haven
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 ￥13,935
￥53,477 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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 ￥11,899
￥29,591 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming Studio| Near Yale| Downtown New Haven
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 ￥14,874
￥41,248 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
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 ￥18,006
￥45,132 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Newly Remodeled with deck. Close to town center
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 ￥16,596
￥43,276 total
includes taxes & fees
Dec 30 - Dec 31
Private Apartment in Southbury 101
TV
Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (9)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
Newly Remodeled 1-BR Close to Everything yet Very Private
Fridge, microwave, oven, stovetop
New Railside Residents

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (1)
"This apartment was the perfect base for visiting family in Wallingford. It had everything we needed, was very clean, and super convenient to downtown cafes and restaurants. The train is a bit loud but to be expected! Will definitely stay again. "
United States
Kelsey S.
New Railside Residents
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 ￥18,006
￥45,132 total
includes taxes & fees
Jan 1 - Jan 2, 2026
All New 1BR with tons of Charm
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 ￥13,950
￥36,593 total
includes taxes & fees
Dec 30 - Dec 31
The Nest At Elm City Flats.
Outdoor dining
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
East Rock
9.6 out of 10, Exceptional, (8)
"Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven"
United States
Derek L.
The price is ￥20,667
￥55,512 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
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 ￥20,354
￥35,854 total
includes taxes & fees
Dec 30 - Dec 31
Spacious 2 Bedroom apartment close to Yale Bowl
Exterior
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
East Rock
10.0 out of 10, Exceptional, (4)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is ￥22,546
￥58,729 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
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

Extended Stay America Suites Shelton Fairfield County

Extended Stay America Suites Shelton Fairfield County

10/10 Excellent
"Very clean, have kitchen, very nice stuff"
Michelia 1-night trip
Posted 1 day ago
Extended Stay America Suites Shelton Fairfield County

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 vacation rentals in Woodbury?

Yes, we offer vacation rentals in Woodbury close to Glebe House Museum and The Gertrude Jekyll Garden, or you can choose a more secluded option if you're looking for a relaxing stay. Our travelers say Woodbury has a good selection of restaurants. Make sure you have time to check out the ski areas and coffeehouses during your trip.

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

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental near Woodbury offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Woodbury?

With 7 Expedia vacation rentals, you're sure 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 vacation rentals like in Woodbury?

Vacation rentals are privately owned properties you can book for a couple days or more in Woodbury. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for small groups.