Woodbury Vacation Rentals

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Jan 2 - Jan 3
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Next weekend
Jan 9 - Jan 11

Our top choices for Woodbury vacation rentals

Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (14)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$145 nightly
The price is $163
Jan 14 - Jan 15
Total with taxes and fees
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

Apartment in Dwight

One bedroom apartment in United States of America, New Haven
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.
$183 nightly
The price is $207
Jan 3 - Jan 4
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
Private kitchen
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in West New Haven

Westville Stay • 2BR • Near Yale • Free Parking
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.
$221 nightly
The price is $221
Jan 6 - Jan 7
Total with taxes and fees
Westville Stay • 2BR • Near Yale • Free Parking
Interior
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Watertown

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
8.6 out of 10, Excellent, (10)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
Jan 3 - Jan 4
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Vacation Home in Shelton

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
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.
$174 nightly
The price is $197
Jan 4 - Jan 5
Total with taxes and fees
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

Vacation Home in Plainville

#26 Beautifully Renovated 2 BR Home
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.
$220 nightly
The price is $237
Jan 24 - Jan 25
Total with taxes and fees
#26 Beautifully Renovated 2 BR Home
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment

Vacation Home in Wallingford Center

Once the old Schools house now a newly furnished Apartment
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.
$271 nightly
The price is $288
Jan 3 - Jan 4
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Torrington

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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.
$303 nightly
The price is $347
Jan 4 - Jan 5
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Cookware/dishes/utensils
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Apartment in East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
9.8 out of 10, Exceptional, (11)
"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.
$259 nightly
The price is $270
Jan 5 - Jan 6
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior
Newly Remodeled with deck. Close to town center

Apartment in Wallingford

Newly Remodeled with deck. Close to town center
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.
$271 nightly
The price is $288
Jan 3 - Jan 4
Total with taxes and fees
Newly Remodeled with deck. Close to town center
Exterior
Cozy One Bedroom Apartment Centrally Located in Southbury

Apartment in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (20)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$110 nightly
The price is $124
Jan 4 - Jan 5
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Exterior
Spacious 2 Bedroom apartment close to Yale Bowl

Apartment in West New Haven

Spacious 2 Bedroom apartment close to Yale Bowl
9.6 out of 10, Exceptional, (69)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
$203 nightly
The price is $230
Jan 3 - Jan 4
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
Interior
Private Apartment in Southbury 101

Apartment in Southbury

Private Apartment in Southbury 101
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.
$244 nightly
The price is $276
Jan 7 - Jan 8
Total with taxes and fees
Private Apartment in Southbury 101
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (7)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$271 nightly
The price is $288
Jan 3 - Jan 4
Total with taxes and fees
All New 1BR with tons of Charm
Outdoor dining
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

Vacation Home in East Rock

Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
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.
$313 nightly
The price is $355
Jan 5 - Jan 6
Total with taxes and fees
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking
Interior
Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale

Apartment in East Rock

Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale
9.4 out of 10, Exceptional, (3)
"Great time with friends."
United States
Ianaliz R.
$298 nightly
The price is $338
Jan 4 - Jan 5
Total with taxes and fees
Golden Gem in the Heart of East Rock | Cozy Comfortable 3BR Near DT | Yale
Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$625 nightly
The price is $641
Jan 22 - Jan 23
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Exterior
Angelica’s safe haven @ west haven

Apartment in West Haven

Angelica’s safe 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
$293 nightly
The price is $334
Jan 3 - Jan 4
Total with taxes and fees
Angelica’s safe haven @ west haven
Interior
The Nest At Elm City Flats.

Apartment in West New Haven

The Nest At Elm City Flats.
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.
$205 nightly
The price is $233
Jan 6 - Jan 7
Total with taxes and fees
The Nest At Elm City Flats.
Fridge, microwave, oven, stovetop
Yale Casa Verde Studio

Apartment in Dwight

Yale Casa Verde Studio
9.6 out of 10, Exceptional, (8)
"Had a great stay!"
United States
Jeffrey C.
$180 nightly
The price is $204
Jan 5 - Jan 6
Total with taxes and fees
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Clean room and friendly staff. "
Diane 1-night trip
Posted 15 hours ago
Holiday Inn Express Southington by IHG

Find out more about Woodbury

Everything you need to know about Woodbury vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodbury vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodbury vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodbury vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodbury. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Woodbury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodbury rentals

At Expedia, we put the best Woodbury vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Woodbury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodbury vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodbury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 8 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.