Woodbury Holiday Rentals

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Holiday Rentals in Woodbury

Indoor spa tub
Spacious Woodbury Home w/ Pool + Hot Tub!
Spacious Woodbury Home w/ Pool + Hot Tub!
On the beach, sun-loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (74)
"Thoroughly enjoyed our stay at Squantz Cottage. Property was well maintained, clean, and convenient. Parking at the cottage can be a little tricky backing out and getting on to the road. An option to park at the main house could be helpful. I would definitely rent again!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
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Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.6 out of 10, Exceptional, (19)
"Wonderful family vacation right on the lake. Memories made, looking forward to returning."
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Private kitchen
Beautiful cozy rooms near hospital and down town area
8.4 out of 10, Very good, (9)
"My friends and I had a great time. Nice and spacious. Thanks for quick reaponces."
The price is AU$379
includes taxes & fees
9 May - 10 May
Beautiful cozy rooms near hospital and down town area
Smart TV, fireplace, ping pong, stereo
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, (9)
"The house had everything we needed and was the perfect winter getaway for our group to celebrate a birthday! Would rent again and again! Amazing property manager who was communicative and gave us all the information we needed. Amazing amenities better than a hotel stay! They have thought of everything - stocked with games and everything you should need for a great vacation! Comfortable and fabulous!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (74)
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Game room
Peaceful apartment on 3.5 acres w/ artist studio.
9.8 out of 10, Exceptional, (10)
"The place was cozy quiet and clean. Exactly what I was looking for."
The price is AU$329
includes taxes & fees
7 May - 8 May
Peaceful apartment on 3.5 acres w/ artist studio.
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (46)
"We enjoyed our stay for the weekend. We had 2 adults and 2 teenagers. Everyone had room to spread out. There is a full flight of stairs to enter the house and a sunroom that would be nice to enjoy in better weather. Thank you for a nice stay!"
Fun Downtown Location
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (6)
"Marianna was super responsive and the house was adorable!"
The price is AU$708
includes taxes & fees
2 June - 3 June
Cozy & Chic Cabin by the Lake, with access to private Beach!
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (33)
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
Fridge, microwave, oven, stovetop
Spacious Victorian Loft
8.4 out of 10, Very good, (6)
"We liked the rental. It was spacious and we appreciated the complimentary coffee. The rental is also a more affordable option in New Haven and not too far away from downtown. It was easy to get in touch with the owner, but it would’ve been helpful if they provided us checkin information in a timely manner. If you’re a light sleeper this might not be the place for you. It’s located by a busy road. There were a lot of cars that were built to be as loud as possible revving their engines into...
The price is AU$293
includes taxes & fees
5 May - 6 May
Spacious Victorian Loft
Exterior
Spacious 2 Bedroom apartment close to Yale Bowl
9.4 out of 10, Exceptional, (46)
"This was the best getaway I've had in recent years. The check-in process was seamless. The property was clean and well maintained. My husband I forgot some toiletries but it wasnt a problem as the bathroom was well stocked! Would definitely stay here again"
The price is AU$361
includes taxes & fees
5 May - 6 May
Spacious 2 Bedroom apartment close to Yale Bowl
Property grounds
NEW 2BR 2B Direct Waterfront Candlewood Lake Home~ Views & Dock~ WINTER SPECIAL!
10.0 out of 10, Exceptional, (14)
"This property was absolutely beautiful, and the property manager Lisa was kind and made herself available if needed. Absolutely plan to come back again."
NEW 2BR 2B Direct Waterfront Candlewood Lake Home~ Views & Dock~ WINTER SPECIAL!
Smart TV, fireplace
The Long View of Candlewood Lake
10.0 out of 10, Exceptional, (5)
"Patricia is an outstanding host with great communication and always pleasantly and quickly responding! The house is just beautiful - clean, comfortable and has clear 'welcome guide'. The location is amazing. We had a great, relaxing time and appreciate it so very much. Everything was perfect! Really want to book again! Thank you!"
The Long View of Candlewood Lake
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, (6)
"This house was exactly as advertised and very charming. The owners were very easy to work with. We had a beautiful view of the lake from the porch. We would stay here again."
Candlewood Lake Retreat with year round views
Outdoor dining
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (21)
"We came up to celebrate a family Birthday, great place to stay, The host has tons of little extras that are really great. Thank you for a great stay."
The Goshen Glass Chalet
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (15)
"From the moment we came we felt right at home! Such a comfortable place to stay! Every morning we were greeted by a beautiful bald eagle on the lake as well as the chitter chatter of birds. For those who have a hard time climbing stairs, this is NOT the place for you. Bedrooms as well as bathrooms are not on the main level. No matter we would definitely want to stay again!"
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
4 bedrooms, iron/ironing board, bed sheets
New Haven Oasis: Steps to Yale & Fine Dining
10.0 out of 10, Exceptional, (1)
"This place is amazing it’s great for a big group or even family lookin for somewhere to stay, even tho the parking spaces in the back was full and no space it was a great stay and will be booking again!!"
The price is AU$705
includes taxes & fees
6 May - 7 May
New Haven Oasis: Steps to Yale & Fine Dining
Exterior
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, (71)
"Great place to celebrate a 40th birthday. Place was clean and comfortable. Great view. Hot tub, lawn games, movie theater, pool table, and more were all great."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
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See all available properties in Woodbury
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.

Other types of properties in Woodbury you may be interested in

Terrace/patio
Hilton Garden Inn Shelton
3.0 star property
7.6 out of 10, Good, (1004)
"Room was clean,staff was friendly. Parts of the room and building could use updating. I usually stay at The Tru by Hilton….I like that there is no carpet on the floor,everything is streamlined,no hidden spaces. This should be considered in all Hiltons. Carpet traps too many germs. "
The price is AU$193
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Shelton
Exterior
Cambria Hotel New Haven University Area
3.0 star property
8.8 out of 10, Excellent, (316)
"Loved "
The price is AU$253
includes taxes & fees
26 May - 27 May
Cambria Hotel New Haven University Area
Lobby lounge
Courtyard by Marriott Waterbury Downtown
3.0 star property
8.2 out of 10, Very good, (1002)
"gOOD SPOT, CLEAN AND EVERYTHING. AC MADE A HELL OF A NOISE. ROOM 210 I THINK OTHER THAN THAT. A+"
The price is AU$157
includes taxes & fees
5 May - 6 May
Courtyard by Marriott Waterbury Downtown
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.

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 favourite 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 depend 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 AU$293 per night. Entering your travel dates in the search wizard might find you 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?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: This holiday home rental outside of Woodbury is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Woodbury?

With 9 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 Lake Quassapaug is a spot to enjoy nature. Other places in town to visit include Pilgrim Mall Shopping Center and Hollow Park.

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.

Recent reviews of Woodbury properties
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