Woodbury Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Woodbury vacation rentals

TV

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 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$273 nightly
The price is $291
Mar 13 - Mar 14
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (2 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
$191 nightly
The price is $217
Mar 13 - Mar 14
Total with taxes and fees
Private Apartment in Southbury 103
1 bedroom, desk, iron/ironing board, WiFi

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
$165 nightly
The price is $187
Mar 13 - Mar 14
Total with taxes and fees
One bedroom in United States of America, New Haven
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"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
$283 nightly
The price is $321
Mar 13 - Mar 14
Total with taxes and fees
Angelica’s safe haven @ west haven
Dining

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 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
$200 nightly
The price is $227
Mar 15 - Mar 16
Total with taxes and fees
Spacious 2 Bedroom apartment close to Yale Bowl
1 bedroom, iron/ironing board, WiFi, bed sheets

Downtown New Haven Escape

Downtown New Haven Escape
Dwight
8.0 out of 10, Very Good, (6 reviews)
"Great place to stay, a little tight for 2 people but good for a single. Well appointed and a great location in the city. Would definitely recommend a stay here."
United States
Michael H.
$240 nightly
The price is $248
Mar 13 - Mar 14
Total with taxes and fees
Downtown New Haven Escape
Outdoor pool

Cozy 1-bedroom apartment in lovely Oxford

Cozy 1-bedroom apartment in lovely Oxford
Oxford
10.0 out of 10, Exceptional, (3 reviews)
"This was my second time staying here. The apartment was immaculately clean and the owner was both professional and personal! The apartment had all the comforts of home, from coffee and snacks in the kitchen to self-care items (e.g., toothbrush, toothpaste, etc). Truly a hidden gem, close to shopping, restaurants, and highways! "
United States
LIsa G.
$142 nightly
The price is $160
Mar 13 - Mar 14
Total with taxes and fees
Cozy 1-bedroom apartment in lovely Oxford
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$113 nightly
The price is $127
Mar 15 - Mar 16
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$284 nightly
The price is $302
Mar 15 - Mar 16
Total with taxes and fees
All New 1BR with tons of Charm
Smart TV

The Sicilian

The Sicilian
West New Haven
9.4 out of 10, Exceptional, (13 reviews)
"Perfect spot for a quick overnight. Cozy and very nicely decorated. "
United States
Jason S.
$208 nightly
The price is $236
Mar 13 - Mar 14
Total with taxes and fees
The Sicilian
Cookware/dishes/utensils

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.8 out of 10, Exceptional, (14 reviews)
"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.
$273 nightly
The price is $285
Mar 18 - Mar 19
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 reviews)
"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
Mar 15 - Mar 16
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
Interior

Pristine, Walkable downtown, Entire 2 Bedroom apartment

Pristine, Walkable downtown, Entire 2 Bedroom apartment
Torrington
10.0 out of 10, Exceptional, (17 reviews)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
$248 nightly
The price is $281
Mar 15 - Mar 16
Total with taxes and fees
Pristine, Walkable downtown, Entire 2 Bedroom apartment
Exterior

Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.0 out of 10, Wonderful, (13 reviews)
"Conveniently located and nice, practically appointed stay for a business trip to work with a collaborator in town."
United States
Jeremy Y.
$177 nightly
The price is $200
Mar 16 - Mar 17
Total with taxes and fees
Bright Downtown Studio near Yale & East Rock!
Bar (on property)

Modern Studio Stay On Howe

Modern Studio Stay On Howe
Dwight
9.0 out of 10, Wonderful, (4 reviews)
"Cute, clean property good for a visit to New Haven for a single or couple. The area is a little noisy, but that's the price you pay for being in close walking distance to everything you'd want to be in close walking distance to! Would definitely stay again. "
United States
Robin A.
$276 nightly
The price is $284
Mar 13 - Mar 14
Total with taxes and fees
Modern Studio Stay On Howe
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
$351 nightly
The price is $398
Mar 13 - Mar 14
Total with taxes and fees
Litchfield Retreat, Wineries, Foliage & Skiing
TV, offices

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds

GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
East Rock
10.0 out of 10, Exceptional, (4 reviews)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
$389 nightly
The price is $441
Mar 15 - Mar 16
Total with taxes and fees
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
1 bedroom, free WiFi, bed sheets

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
New Milford
8.0 out of 10, Very Good, (1 review)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
$170 nightly
The price is $193
Mar 13 - Mar 14
Total with taxes and fees
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
Desk, iron/ironing board, WiFi, bed sheets

Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.6 out of 10, Exceptional, (10 reviews)
"Had a great stay!"
United States
Jeffrey C.
$165 nightly
The price is $187
Mar 15 - Mar 16
Total with taxes and fees
Yale Casa Verde Studio
Interior

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.6 out of 10, Exceptional, (9 reviews)
"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "
United States
Joan S.
$241 nightly
The price is $273
Mar 16 - Mar 17
Total with taxes and fees
The Nest At Elm City Flats.
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

Hyatt House Shelton

Hyatt House Shelton

6/10 Okay
"The heat was variable and shower was like warm at best. Overall the hotel was nicely appointed but coffee was awful. "
Deirdre 1-night trip
Posted 1 hour ago
Hyatt House Shelton

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 $127 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 Flanders Nature Center, 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?

Cultural attractions include Glebe House Museum and The Gertrude Jekyll Garden, whereas Flanders Nature Center is a spot to enjoy nature. Other places in town to visit include Pilgrim Mall Shopping Center and Hollow Park.

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.