Woodbury Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Woodbury vacation rentals

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
$124 nightly
The price is $139
Mar 3 - Mar 4
Total with taxes and fees
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
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
$287 nightly
The price is $325
Mar 3 - Mar 4
Total with taxes and fees
Angelica’s safe haven @ west haven
Fridge, microwave, oven, stovetop

One bedroom apartment in United States of America, New Haven

One bedroom apartment in United States of America, New Haven
Dwight
8.6 out of 10, Excellent, (4 reviews)
"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.
$180 nightly
The price is $204
Mar 3 - Mar 4
Total with taxes and fees
One bedroom apartment in United States of America, New Haven
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.
$233 nightly
The price is $241
Mar 3 - Mar 4
Total with taxes and fees
Downtown New Haven Escape
Smart TV

#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
$302 nightly
The price is $322
Mar 3 - Mar 4
Total with taxes and fees
#23 *COMFORT & LUXURY* 3 BR/2 BA House
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.
$204 nightly
The price is $232
Mar 3 - Mar 4
Total with taxes and fees
The Nest At Elm City Flats.
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.
$287 nightly
The price is $305
Mar 3 - Mar 4
Total with taxes and fees
All New 1BR with tons of Charm
Interior

Cozy & Serene Cabin with Fireplace, Ski Nearby!

Cozy & Serene Cabin with Fireplace, Ski Nearby!
Bethlehem
9.8 out of 10, Exceptional, (40 reviews)
"Very comfortable property. The host had thought of everything!"
United States
Jennifer Y.
$375 nightly
The price is $425
Mar 8 - Mar 9
Total with taxes and fees
Cozy & Serene Cabin with Fireplace, Ski Nearby!
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
#26 Beautifully Renovated 2 BR Home
2 bedrooms, desk, iron/ironing board, free WiFi

#37 - Luxury Collection

#37 - Luxury Collection
Stratford
8.0 out of 10, Very Good, (4 reviews)
"We enjoyed the coziest getaway at this property. Newly renovated, clean and tucked away without being accessible to local attractions. "
United States
Sarah T.
#37 - Luxury Collection
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.
$327 nightly
The price is $345
Mar 14 - Mar 15
Total with taxes and fees
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
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
$111 nightly
The price is $125
Mar 6 - Mar 7
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Apartment (1 Bedroom) | Private kitchen | Fridge, coffee/tea maker

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University
3.0 star property
Downtown New Haven
Landing Furnished Apartment Near Yale University
Interior

Pristine, Walkable downtown, Entire 2 Bedroom apartment

Pristine, Walkable downtown, Entire 2 Bedroom apartment
Torrington
10.0 out of 10, Exceptional, (16 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.
$230 nightly
The price is $261
Mar 11 - Mar 12
Total with taxes and fees
Pristine, Walkable downtown, Entire 2 Bedroom apartment
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.
$173 nightly
The price is $196
Mar 3 - Mar 4
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

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.
$202 nightly
The price is $230
Mar 21 - Mar 22
Total with taxes and fees
Private Apartment in Southbury 103

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 3 - Mar 4
Total with taxes and fees
GreenN'Groovy: East Rock 5 mins to DT|Yale 5 beds
Property grounds

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
$236 nightly
The price is $267
Mar 3 - Mar 4
Total with taxes and fees
River Overlook - Check the view from your deck!
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 3 - Mar 4
Total with taxes and fees
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
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

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

10/10 Excellent
"Was great"
EVELYN 1-night trip
Posted 3 days ago
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

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 $125 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?

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

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.