Woodbury Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Woodbury vacation rentals

Exterior

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
The price is ￥33,968
￥74,658 total
includes taxes & fees
Apr 2 - Apr 3
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is ￥20,714
￥51,084 total
includes taxes & fees
Apr 2 - Apr 3
Angelica’s safe haven @ west haven
House (3 Bedrooms) | Interior

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
3.0 star property
Oakville
The price is ￥34,921
￥80,911 total
includes taxes & fees
Apr 2 - Apr 3
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Fridge, microwave, oven, stovetop

#27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is ￥43,492
￥87,000 total
includes taxes & fees
Apr 3 - Apr 4
#27- Luxury Collection
TV, offices

PinkN'Peachy: East Rock 5 Mins from DT|Yale 5 beds

PinkN'Peachy: East Rock 5 Mins from DT|Yale 5 beds
East Rock
10.0 out of 10, Exceptional, (4 reviews)
"The house was super clean and perfect for a larger group. Also, the location was convenient to nearby attractions."
United States
Luke B.
The price is ￥34,199
￥75,166 total
includes taxes & fees
Apr 2 - Apr 3
PinkN'Peachy: East Rock 5 Mins from DT|Yale 5 beds
Exterior detail

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (35 reviews)
"Stunning property!!"
United States
Samantha
The price is ￥43,651
￥75,913 total
includes taxes & fees
Apr 6 - Apr 7
Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥30,952
￥39,404 total
includes taxes & fees
Apr 5 - Apr 6
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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.
#23 *COMFORT & LUXURY* 3 BR/2 BA House
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.
The price is ￥28,254
￥51,262 total
includes taxes & fees
Apr 8 - Apr 9
River Overlook - Check the view from your deck!
Exterior

Cozy Gem: East Rock |King Bed| Near DT|Yale 3 beds

Cozy Gem: East Rock |King Bed| Near DT|Yale 3 beds
East Rock
9.6 out of 10, Exceptional, (8 reviews)
"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 ￥33,968
￥74,658 total
includes taxes & fees
Apr 2 - Apr 3
Cozy Gem: East Rock |King Bed| Near DT|Yale 3 beds
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)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveler
The price is ￥15,182
￥42,102 total
includes taxes & fees
Apr 2 - Apr 3
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is ￥23,413
￥110,418 total
includes taxes & fees
Apr 9 - Apr 10
CT Gate House Goshen CT, Gate House Goshen CT
Outdoor dining

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (63 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is ￥49,524
￥82,230 total
includes taxes & fees
Apr 21 - Apr 22
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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, (70 reviews)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is ￥14,286
￥28,730 total
includes taxes & fees
Apr 9 - Apr 10
Spacious 2 Bedroom apartment close to Yale Bowl
Property grounds

3-Bedroom Cabin Getaway With Rustic Charm

3-Bedroom Cabin Getaway With Rustic Charm
Cornwall
8.4 out of 10, Very Good, (6 reviews)
"Absolutely beautiful cottage exactly as pictured inside and out. "
United States
Michaela C.
The price is ￥34,375
￥86,596 total
includes taxes & fees
Apr 2 - Apr 3
3-Bedroom Cabin Getaway With Rustic Charm
Fridge, microwave, oven, stovetop

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is ￥46,286
￥59,461 total
includes taxes & fees
Apr 6 - Apr 7
The Jefferson Guest House, Spacious, Special Views
Smart TV

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, (17 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is ￥18,218
￥31,498 total
includes taxes & fees
Apr 19 - Apr 20
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Lobby

Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very Good, (8 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
The price is ￥17,857
￥39,227 total
includes taxes & fees
Apr 7 - Apr 8
Spacious Bohemian Nook
Interior

New Railside Residents

New Railside Residents
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"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.
The price is ￥18,254
￥44,325 total
includes taxes & fees
May 1 - May 2
New Railside Residents
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.
The price is ￥18,254
￥44,167 total
includes taxes & fees
May 1 - May 2
Once the old Schools house now a newly furnished Apartment
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

Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton

10/10 Excellent
"Excellent breakfast, spacious room, and ample parking "
Faye 3-night trip
Posted 8 hours ago
Hampton Inn by Hilton Shelton

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:

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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 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 Lake Quassapaug 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.