Woodbury Vacation Rentals

Vacation Rentals in Woodbury

Spacious Woodbury Home w/ Pool + Hot Tub!
Indoor spa tub
Spacious Woodbury Home w/ Pool + Hot Tub!
Spacious Woodbury Home w/ Pool + Hot Tub!
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 75 reviews
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
On the beach, sun loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 59 reviews
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
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Fun Downtown Location
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, 49 reviews
"Overall a good experience."
Fun Downtown Location
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, 17 reviews
"The property is lovely and well prepared for guests. The location is wonderful. One of our highlights was watching a bald eagle soar over the lake."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Property grounds
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, 6 reviews
"Great property, very clean and host was quick to reply. We were impressed with the amenities available (most places don’t have detergent, etc) and the view was amazing! We didn’t have time to go to the dock but it looked very nice! Wish we had time to stay longer. We will definitely try to stay there again for our next family event"
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, 8 reviews
"We’d go back."
The price is $225
$457 total
includes taxes & fees
Jun 11 - Jun 12
Cozy & Chic Cabin by the Lake, with access to private Beach!
Beautiful cozy rooms near hospital and down town area
Private kitchen | Fridge, microwave, oven, stovetop
Beautiful cozy rooms near hospital and down town area
8.4 out of 10, Very Good, 10 reviews
"People were very nice and welcoming. Area looks questionable but the place itself is very comfortable, clean and enjoyable."
The price is $109
$247 total
includes taxes & fees
Jun 13 - Jun 14
Beautiful cozy rooms near hospital and down town area
Guest Cottage on Country Estate
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, 33 reviews
"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
New Haven Oasis: Steps to Yale & Fine Dining
4 bedrooms, iron/ironing board, bed sheets
New Haven Oasis: Steps to Yale & Fine Dining
10.0 out of 10, Exceptional, 3 reviews
"Was perfect for my family of 8 for the few days we were in New Haven for my PA graduation. Close to all main dining ! Host was very responsive on all questions I had !"
The price is $199
$503 total
includes taxes & fees
Jun 11 - Jun 12
New Haven Oasis: Steps to Yale & Fine Dining
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.8 out of 10, Exceptional, 21 reviews
"The property was as described and the living space was perfect for our visit. The deck and views are amazing. If staying at this property, you just need to be aware that it is very difficult getting luggage and groceries into the property. You have to go down a long flight of stairs, walk down a very steep driveway and then go down another flight of stairs. Once you are in, bedroom access requires that you go up or down additional stairs."
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, table tennis, stereo
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, 11 reviews
"We absolutely loved the house! This was the perfect place to bring my adult children together for a weekend away. The rooms were beautiful, beds were super comfortable, and house nicely decorated. There were spots for smaller groups to sit together and hang out or to come together and chat. The hot tub was appealing to my 20somethings but it was rainy- next time!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, 18 reviews
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
The price is $470
$961 total
includes taxes & fees
Jun 13 - Jun 14
Lakeview Estate - Chef's Kitchen - NYC Getaway
Candlewood Lake Retreat with year round views
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, 7 reviews
"We thoroughly enjoyed our time at this wonderful little home. It was pleasantly quiet and secluded, but was just minutes away from some wonderful restaurants and just a short walk to the lake. The hosts were just so responsive and accommodating. We also had one day of rainy weather, which afforded us the opportunity to simply stay in and relax. The kitchen had all of the amenities we could have asked for. The seating area on the deck was spacious and comfortable. We are certainly looking forward...
Candlewood Lake Retreat with year round views
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
Exterior
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
10.0 out of 10, Exceptional, 72 reviews
"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!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, 20 reviews
"We were in area from Uk visiting friends who live not far away. So this little home was just ideal for us. Weather improved on the day we left so we didnt sit outside by the lake but we did enjoy watching the birds and fish."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Peaceful apartment on 3.5 acres w/ artist studio.
Game room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, 11 reviews
"Cute."
The price is $140
$213 total
includes taxes & fees
Jun 18 - Jun 19
Peaceful apartment on 3.5 acres w/ artist studio.
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, 17 reviews
"Gorgeous, as advertised!"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, 7 reviews
"This is a charming house that actually is even better than the photos! Spotless and organized. Kitchen is perfectly stocked. Came with a bag of nice Italian coffee, Kurig and teas with refrigerated creamer. Bed was terrific and large. AC and Heat easy to use. Easy to find and surrounded by everything you need, like food, coffee, bagels, restaurants."
Lakefront Home, Close to Mt Southington!
Traveling Nurse or Business Professional
Exterior
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, 7 reviews
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
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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

Courtyard by Marriott Waterbury Downtown
Lobby lounge
Courtyard by Marriott Waterbury Downtown
3.0 star property
8.2 out of 10, Very Good, 1,016 reviews
"Coffee shop was supposed to open at 7 am on Sundays and when asked for a coffee at 7:15 am to the employee said that we have to wait 15 minutes to order it."
The price is $93
$107 total
includes taxes & fees
Jun 16 - Jun 17
Courtyard by Marriott Waterbury Downtown
Holiday Inn Express Southington, an IHG Hotel
Exterior
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very Good, 1,009 reviews
"It was clean "
The price is $142
$163 total
includes taxes & fees
Jun 30 - Jul 1
Holiday Inn Express Southington, an IHG Hotel
Cambria Hotel New Haven University Area
Exterior
Cambria Hotel New Haven University Area
3.0 star property
8.8 out of 10, Excellent, 354 reviews
"Clean, elegant design, lots of natural light, window seats in the bedroom. Very gracious and helpful front desk staff"
The price is $135
$155 total
includes taxes & fees
Jun 16 - Jun 17
Cambria Hotel New Haven University Area
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 vacation rentals

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

Woodbury vacation 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 low season months. For more hustle and bustle, you may prefer to visit Woodbury in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $109 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodbury rentals

At Expedia, we put the best Woodbury vacation 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 vacation.

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 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?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: This vacation home rental near Woodbury is located on the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.

Recent reviews of Woodbury properties
Expedia verified reviews

The Blake Hotel

The Blake Hotel

5/5 Excellent
Nice vibe
"The lobby and bar/restaurant have a very appealing look, very nicely decorated as are the hallways. Room was spacious and the bed was very comfortable.I would say that the bathroom lighting is inadequate for putting on makeup, way too dark in there. Also there was no desk light either which was needed. Floor was a bit sticky which made me wonder what was used to clean it. Other than that, very nice hotel. "
A verified traveler stayed at The Blake Hotel
Posted 18 hours ago
The Blake Hotel