Woodbury Holiday Rentals

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Holiday Rentals in Woodbury

Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.

Woodbury
10.0 out of 10, Exceptional, (1)
"My wife and I decided at the last minute to get away this place fit this it is a closed up ski resort the owner is so nice he actually came out went over everything with us the night we arrived the stay was amazing wood stove was the best we made a pallet on floor by the wood stove was just the best Seymour was the best and did everything to make your stay the best"
United States
Edward B.
Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Brookfield
9.6 out of 10, Exceptional, (4)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (16)
"Excellent stay !!!! Everything was perfect. Communication was phenomenal.!!!!"
United States
daniellle
The price is NZ$226
includes taxes & fees
23 Nov - 24 Nov
New One Bedroom Apartment Centrally Located in Southbury

Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!

West River
8.4 out of 10, Very good, (13)
"Perfect place to stay for me and my friends for yale reunion weekend! "
United States
Katie H.
Charming Historic 2BR Retreat in New Haven – Cozy Stay Near Yale & Downtown!

Peaceful Vintage Home with Private Lake in Redding, CT.

2.0 star property
Redding
10.0 out of 10, Exceptional, (2)
"Property was beautiful in a very quiet and peaceful area. Our host Kadriia was so amazing and would respond so quickly to any questions we had and communicated clearly. My wife and our friends had a Halloween themed wedding party for our friends who couldn’t make it to the actual wedding and we couldn’t have had a better time. "
United States
Connor K.
The price is NZ$1,033
includes taxes & fees
16 Nov - 17 Nov
Peaceful Vintage Home with Private Lake in Redding, CT.

Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

2.0 star property
West New Haven
9.0 out of 10, Wonderful, (2)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is NZ$227
includes taxes & fees
16 Nov - 17 Nov
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Charming Studio| Near Yale| Downtown New Haven

Downtown New Haven
9.0 out of 10, Wonderful, (10)
"Nice location in downtown New Haven. The room itself is nice and convenient. The window near the bed does not close because there is a large tube going through the window with tape around it. On a chilly day/night this is not comfortable and there is nothing one can do since the window does not close. You can also hear everything going on outside because the window does not close. Bedsheets were not clean either. Contacted the host about the window and bedsheets and the host gave me the...
United States
Noel
The price is NZ$387
includes taxes & fees
16 Nov - 17 Nov
Charming Studio| Near Yale| Downtown New Haven

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Northwest Harwinton
8.6 out of 10, Excellent, (27)
"Clean, quite stores only 8 minutes away. "
United States
Mindy H.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

New Fairfield
10.0 out of 10, Exceptional, (14)
"Was a great find. Updated, spacious and clean."
United States
Paul B.
The price is NZ$915
includes taxes & fees
16 Nov - 17 Nov
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Cheshire
9.2 out of 10, Wonderful, (11)
"Very nice location in a country setting. Saw deer in the backyard every morning. Very clean and accurate description of the property. Friendly hosts who supplied everything we needed. Would stay here again. Highly recommend."
United States
Eileen A.
The price is NZ$287
includes taxes & fees
16 Nov - 17 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

Danbury
10.0 out of 10, Exceptional, (24)
"Beautiful house with amazing views. Can’t wait to stay again. Great location too! Close to everything (shopping/food/activities) but located on a very quiet dead end. Owners were easy to communicate with and very friendly. "
United States
Mary M.
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

The Sun Filled Cozy Creamery

Plainville
8.8 out of 10, Excellent, (24)
"Pleasure staying here. "
United States
Jesse H.
The price is NZ$483
includes taxes & fees
21 Nov - 22 Nov
The Sun Filled Cozy Creamery

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth
9.8 out of 10, Exceptional, (39)
"Owners were there, helpful, all in all very good"
United States
Walter B.
Cozy Lakefront Bungalow w firepit/dock/kayaks

Fun Downtown Location 2nd flr

Southington
9.8 out of 10, Exceptional, (78)
"Nice place, comfy beds, good amenities, clean. Good restaurants."
United States
Tanya C.
Fun Downtown Location 2nd flr

Room-plaid Room 3min From Yale Univ

3.0 star property
Newhallville
10.0 out of 10, Exceptional, (1)
"The owner is great and made great accommodations for our stay, the price was wonderful. The neighborhood maybe wasent the nicest but thats kinda out of his control."
United States
Colby
Room-plaid Room 3min From Yale Univ

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 NZ$346
includes taxes & fees
16 Nov - 17 Nov
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Modern Comfort - 2BR Spacious Suite - Near Yale

Newhallville
10.0 out of 10, Exceptional, (1)
"Apartment was cozy and the kitchen fully functional. The host was very nice, responsive and thoughtful. We would definitely recommend or stay again ourselves. "
United States
Sochi N.
Modern Comfort - 2BR Spacious Suite - Near Yale

All New 1BR with tons of Charm

Wallingford Center
9.8 out of 10, Exceptional, (6)
"This is a very nice updated one-bedroom apartment in a central location. Restaurants are within walking distance. The building has an elevator. The kitchen has everything you need. I enjoyed my stay. Just one caveat: the train tracks run just behind the building. The trains aren’t constant, but they do blow their horn at the intersection. I brought earplugs, and the noise didn’t keep me from sleeping "
United States
Karen D.
The price is NZ$455
includes taxes & fees
17 Nov - 18 Nov
All New 1BR with tons of Charm

Yale Casa Azul Studio

Dwight
6.0 out of 10, (3)
"It was really nice place, people were so nice, good area"
United States
Sophia T.
The price is NZ$387
includes taxes & fees
16 Nov - 17 Nov
Yale Casa Azul Studio

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Watertown
9.6 out of 10, Exceptional, (15)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
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

Find out more about Woodbury

Everything you need to know about Woodbury holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodbury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woodbury holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodbury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodbury holiday rentals we have selected for you start as low as NZ$226 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodbury rentals

At Expedia, we put the best Woodbury holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Woodbury?

Yes, there are holiday rentals in Woodbury close to Glebe House Museum and The Gertrude Jekyll Garden, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Woodbury has a good selection of restaurants. Make sure you have time to check out the ski areas and coffee shops during your trip.

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

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Woodbury offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Woodbury?

With 8 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Woodbury?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodbury. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.