A park with a paved walkway, trees, and historic buildings in the background.

Woodbury Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18
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Top Woodbury Hotel Reviews

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"I was pleasantly surprised with this property. I arrived and first thing I noticed was a huge parking lot. Even more pleasing are the parking spaces, which had ample room to park my mid size car. It is an actual pet peeve when a property provides very little space to park, to where cars are parked so closely together, there's a good chance that some other guests will wildly open their car doors and chip the paint from your vehicle.. This was a sign of good things to come. The lobby area and overall property was just as big. It was much bigger than I anticipated. The staff was super friendly and accommodating to my needs and answered my questions upon check in. They key cards worked (last property I stayed had terrible key cards, preventing entry to room). The room was clean, spacious, and in excellent condition. All of the necessities were there to use. The bed was comfortable. There was a bar across the front desk but I did not use it. A quick glance of their menu and business hours were available to see in the elevator and other areas. It seemed well kept. There's a buffet breakfast which was reasonably priced. The food was actually decent in comparison to other properties that offer breakfast. I did not use any other their other on site serviess such as laundry or fitness room. I enjoyed my time at this property, which I never have known about prior to my stay. This is in fact the longest, detailed review I've written, which means I'd gladly return here again!"
Marcus 1-night trip
Posted 2 hours ago
Wyndham Southbury

Find out more about Woodbury

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Woodbury. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 9 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 Lake Quassapaug and Pilgrim Mall Shopping Center.

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.