Woodbury Holiday Rentals

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Holiday Rentals in Woodbury

Our top choices for Woodbury holiday rentals

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Cozy Country Cottage

2.0 star property
9.0 out of 10, Wonderful, (7)
"Very accommodating and understanding host.They are warm and willing to listen and make your stay as comfortable as possible. Trent and his family will go out of their way to make the stay memorable.. I would highly recommend the stay at this accommodation to everyone. A home away from home."
The price is NZ$443
includes taxes & fees
17 Sept - 18 Sept
Cozy Country Cottage

Charming Studio| Near Yale| Downtown New Haven

9.0 out of 10, Wonderful, (4)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is NZ$341
includes taxes & fees
16 Sept - 17 Sept
Charming Studio| Near Yale| Downtown New Haven

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

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Yale Casa Verde Studio

10.0 out of 10, Exceptional, (4)
"Had a great stay!"
The price is NZ$352
includes taxes & fees
21 Sept - 22 Sept
Yale Casa Verde Studio

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

8.8 out of 10, Excellent, (22)
"We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

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

8.8 out of 10, Excellent, (24)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Angelica’s safe haven @ west haven

10.0 out of 10, Exceptional, (5)
"This place was perfect for our weekend trip to New Haven. Angelica was a great Host, and communicated timely and clear. I would stay again if I ever come back to New Haven. "
The price is NZ$563
includes taxes & fees
16 Sept - 17 Sept
Angelica’s safe haven @ west haven

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (46)
"Wonderful! Elizabeth and John made everything seamless and enjoyable. Terrific location! "
The price is NZ$2,380
includes taxes & fees
17 Sept - 18 Sept
Waterfront Family Retreat on Candlewood Lake

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (47)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (30)
"Happy to have rebooked!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway

Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

10.0 out of 10, Exceptional, (13)
"Beautiful location and lots of space for a large group. This rental is really about the outdoor space and activities. Would love to return!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

10.0 out of 10, Exceptional, (3)
"Perfect for families."
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Family Gem on Dyer Street

The price is NZ$1,578
includes taxes & fees
23 Sept - 24 Sept
Family Gem on Dyer Street

Spacious Lakeside Hideaway

10.0 out of 10, Exceptional, (1)
"We enjoyed a very relaxing two-night getaway in Pat’s ground floor apartment. The views are gorgeous and the apartment is set up beautifully, with lovely art and numerous fascinating cookbooks. We found the bed incredibly comfortable. While we had all we needed for our light cooking, the kitchenware offerings were extensive. The Newtown General Store, recommended by Pat, is a must for delicious and inexpensive sandwiches. After a bike ride from Monroe to Trumbull, we had a great time sipping...
Spacious Lakeside Hideaway

Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area

10.0 out of 10, Exceptional, (5)
"Everything was amazing "
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area

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

10.0 out of 10, Exceptional, (60)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is NZ$751
includes taxes & fees
16 Sept - 17 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

10.0 out of 10, Exceptional, (79)
"We stayed for a birthday weekend with a few other couples and had a great time. There is plenty of space for everyone to spread out and each 'area' of the house is incredibly comfortable (especially the movie theater). If you need anything there are plenty of stores close by and the area is very safe. Overall, no complaints and would recommend to anyone looking for a getaway."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

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."
The price is NZ$329
includes taxes & fees
16 Sept - 17 Sept
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"we couldn't ask for a better place. It had all the conveniences we like. The host did a great job here."
The Goshen Glass Chalet
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

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$329 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 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.