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Compare 225 Vacation Homes in Woodbury with updated reviews, rates, and availability.

Private Annex/Former Artist Studio
Room
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (46)
"The owner greeted us the first night. Very pleasant and super friendly. The space is beautiful and the fact that it was once an artist's studio for me made it even more special. The nearby lake is gorgeous. We brought our dog and she was very relaxed and comfortable for the stay. I thoroughly enjoyed the property and our mini vacation! "
Private Annex/Former Artist Studio
Lakeview Estate - Chef's Kitchen - NYC Getaway
Terrace/patio
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (23)
"Fantastic place! Beautiful views, lots of room, comfy beds, clean. There was 10 of us and it was a delight. Highly recommend it. "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Our group of 2 couples enjoyed our week in the Hudson Valley area. We all commented on the excellent beds and pillows, the view of the lake from the house and the quiet of the neighborhood. Would stay here again."
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Tranquil Litchfield Connecticut Retreat".
Terrace/patio
Tranquil Litchfield Connecticut Retreat".
9.8 out of 10, Exceptional, (6)
"They obviously care very much about the place. Everything was pristine. Beds were comfortable. Location was convenient. Everything was as advertised. "
The price is AED 808
AED 1,160 total
includes taxes & fees
14 Nov - 15 Nov
Tranquil Litchfield Connecticut Retreat".
Lakefront Home, Close to Mt Southington!
Wolcott Vacation Rental | 3BR | 2BA | 1,176 Sq Ft | Stairs Required
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (13)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
The Goshen Glass Chalet
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (27)
"Wanted to visit my son in Litchfield around Halloween with my 2 teenaged granddaughters. The Goshen Glass Chalet was the perfect place for our visit. Loved every detail. "
The Goshen Glass Chalet
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Living Room
Charming 3BR Hilltop House, Newly Remodeled with Arcade
10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Cozy 2 bedroom home located minutes from downtown
Room
Cozy 2 bedroom home located minutes from downtown
9.6 out of 10, Exceptional, (23)
"We found this house to be the perfect spot just outside downtown New Haven. We did need a car, but the location was great. We had easy access to main roads, downtown, and there was sufficient local restaurants and stores for stocking the house. The unit was as it appeared and the host was responsive and helpful when needed."
Cozy 2 bedroom home located minutes from downtown
Gather your family at this country estate
Living area
Gather your family at this country estate
10.0 out of 10, Exceptional, (3)
"This is an older home with charm. Lots of room, and while just six of us stayed, it appears more could be accommodated with inflatable mattresses. We enjoyed sitting outside by the simple fire pit one night. I would encourage the owners to put an outside light in the back as I stumbled on the stairs twice but that’s really the only issue. We are so sorry we misplaced one of the two keys,please send us a bill for a copy if you don’t find it. Thank you!"
Gather your family at this country estate
Near Yale 8 beds Gaming Room
Exterior
Near Yale 8 beds Gaming Room
The price is AED 2,020
AED 4,035 total
includes taxes & fees
20 Nov - 21 Nov
Near Yale 8 beds Gaming Room
NEW-Another Fun Downtown Location 1st floor
Exterior detail
NEW-Another Fun Downtown Location 1st floor
2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Property grounds
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
2.0 star property
10.0 out of 10, Exceptional, (2)
"Amazing view amazing hot tub very relaxing "
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Sunset on the lake.
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
10.0 out of 10, Exceptional, (105)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
10.0 out of 10, Exceptional, (41)
"The Hosts were extremely nice and helpful in the entire process. They answered questions and helped me understand the offering so I could book with confidence, The home is spacious and welcoming in design. Generous spaces throughout including a very nice kitchen and a basement gameroom that was very enjoyable. The outside seating areas were outstanding including a wonderful lakefront area to sit and enjoy the views. Book with confidence for a great experience. Dan and Kit "
Candlewood Lake Grand Waterfront Oasis: A Luxurious Family Retreat
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, (23)
"Wonderful house. Comfortable beds. Amazing lake view. Great location. We stayed for 3 nights and enjoyed it so much."
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Traveling Nurse or Business Professional
Exterior
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, (7)
"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
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (40)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Terrace/patio
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (14)
"Beautiful property— even more than the pictures (which is often rare). Quiet, scenic, and spacious. Communication with the host was very good and helpful."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Property grounds
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
9.0 out of 10, Wonderful, (4)
"Main and only complaint was that had to keep playing with the handle of the toilet every time flushed or it would keep running. Very annoying. And just felt food items. ( pancake mix ect) should be tossed. Safety and health purposes . Otherwise very enjoyable. Stay"
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
5,100 Sq. Ft. Swiss Chalet-sixteen beautiful, private acres-Perfect for Holidays
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
10.0 out of 10, Exceptional, (8)
"The hosts were wonderful and so welcoming. The house had everthing you could want and more! It was the perfect location for my family to relax before and get ready the day of my daughter's wedding. "
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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Other property types in Woodbury

Spacious Woodbury Home w/ Pool + Hot Tub!
Woodbury Vacation Rental | 4BR | 3BA | 3,321 Sq Ft | Stairs Required for Access
Spacious Woodbury Home w/ Pool + Hot Tub!
Spacious Woodbury Home w/ Pool + Hot Tub!
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Our group of 2 couples enjoyed our week in the Hudson Valley area. We all commented on the excellent beds and pillows, the view of the lake from the house and the quiet of the neighborhood. Would stay here again."
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Breathtaking lake views while grilling out and soaking up the sun with family!
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
9.4 out of 10, Exceptional, (14)
"This house does have a lovely view that allowed us to take in the changing leaves off the reflection of the lake. The house is smaller than it appears in the photos and not quite as comfortable to just hang out, at least inside.The couch fits three, but there aren't other chairs in the living area. There are great little outside areas though. Communication with Katherine was great. Previous tenants had broken the washer which was a drag and due to weather (drought conditions) we couldn't use...
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
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.