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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 236 Vacation Homes in Woodbury with updated reviews, rates, and availability.

Escape to a Celebrity Chef's Waterfront Lake House

Escape to a Celebrity Chef's Waterfront Lake House

10.0 out of 10, Exceptional, (1)
Escape to a Celebrity Chef's Waterfront Lake House
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Property grounds

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (22)
"We made happy memories over a cold January weekend. We cooked together, sat around the fire, played games and dozed in comfortable beds with high quality linens. We enjoyed the view of the water and the twinkling lights on the property at night. The steam shower was divine. If you like cooking, bring good knives, a veggie peeler and good pans. Plenty of glassware and dishes and some cookware provided. "
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
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, (16)
"My time spent at the lake house with my family was unforgettable. Nestled along the serene shoreline, the house offered stunning lake views from every window. Mornings began with coffee on the spacious deck, watching the sun rise over the water. Days were filled with family fun. The house itself was cozy yet modern, with plush furnishings, a crackling fireplace, and a fully-equipped kitchen where we cooked meals together. Evenings were spent playing board games, hanging out by the fire pit. It...
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Terrace/patio

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.
The Goshen Glass Chalet

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (31)
"Our weekend stay here was absolutely amazing. The house was spotless and had all the conveniences of home. The owner was quick to respond to any questions that we had. The hot tub was absolutely a selling point for us. We were so relaxed in this spacious house from the fully stocked kitchen, to the bathrobes, to the Awesome outside, screened in porch. The kids had a blast in the basement with ping pong, and the games stocked in the closet. I would love to come back in the spring and summer to...
The Goshen Glass Chalet
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT
Exterior

Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

2.0 star property
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT
NEW-Another Fun Downtown Location 1st floor
Exterior

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (9)
"It was a nice quiet valuable time spent together .just what we needed for that very special memorable time. Thanks."
NEW-Another Fun Downtown Location 1st floor
Near Yale with Game Room
Exterior

Near Yale with Game Room

The price is AED 1,969
AED 4,205 total
includes taxes & fees
24 Feb - 25 Feb
Near Yale with Game Room
Renovated, one level home in an excellent location
Fully equipped kitchen. (1)

Renovated, one level home in an excellent location

10.0 out of 10, Exceptional, (39)
"We had a great stay! "
Renovated, one level home in an excellent location
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, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (25)
"Great place, great service!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Exterior

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"We traveled to CT with my parents for the week. Richie and Helen were very gracious. Their home is beautiful. They had everything a family would need on vacation. We needed to attend an event and I asked Richie if they had an iron/ironing board. They did not. Richie was at the door 30 minutes later with the items! The temperature dropped about 30 degrees while we were there. We texted about heat and they responded within minutes and turned on heat. We were very comfortable. My parents are 80...
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Lakeside luxury: beautiful, relaxing 4 bedroom home
Sit back and relax!

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (18)
"We enjoyed the lovely view of the lake and our wonderful, brisk walks in the neighborhood. The spacious and well-appointed lake home was perfect of our family with young adult children. We loved this beautiful, comfortable and entertaining home on the lake and hope to return."
Lakeside luxury: beautiful, relaxing 4 bedroom home
Hidden Gem: Newly Remodeled 5-Bedroom Haven with Central AC in New Haven
Exterior

Hidden Gem: Newly Remodeled 5-Bedroom Haven with Central AC in New Haven

Hidden Gem: Newly Remodeled 5-Bedroom Haven with Central AC in New Haven
Cozy Lakefront Bungalow w firepit/dock/kayaks
Covered Mahogany deck, perfect for drinks and hanging out

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (25)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern Renovations and Family Fun
Cottage at Sunny Day, multiple levels for multiple views of the lake

Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern Renovations and Family Fun

9.8 out of 10, Exceptional, (33)
"I spent a week at the Cottage at Sunny Day in mid January and it was just what I was looking for. I wanted a quiet, relaxing retreat in a beautiful location. The house was immaculate and very comfortable. Everything was provided, and there was a great fireplace and a beautiful view of Lake Taunton. Jenna and Tony were very nice and easy to deal with and made sure that everything was perfect. It would be a great stay at any time, but would be especially nice in the warm weather with direct access...
Lakefront Cottage with Private Dock, Kayaks, Stunning Lake Views, Modern Renovations and Family Fun
The Connecticut Chalet - On 5 Acres!
Interior

The Connecticut Chalet - On 5 Acres!

10.0 out of 10, Exceptional, (2)
"If you’re looking for a relaxing, unique/fun home this is it!! The host was amazing & left no questions to ask. The home is fully stocked with all your needs from cooking utensils, wood to start a warm fire & even games for in between time. The bedrooms are cozy and the beds are super soft. The deck & sun room/dining room was a fav, the views are amazing. I would certainly recommend and even stay here again. Thank you "
The Connecticut Chalet - On 5 Acres!
The Art House: 5-Acre, Private Getaway with Fireplace
Interior

The Art House: 5-Acre, Private Getaway with Fireplace

9.8 out of 10, Exceptional, (13)
"Great weekend "
The Art House: 5-Acre, Private Getaway with Fireplace
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
Exterior

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

10.0 out of 10, Exceptional, (1)
"Beautiful home, worked well for 10 adults. Great hosts, well stocked with everything we needed. Clean, comfy, cozy! Would recommend to friends and family! "
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer
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

Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.
Interior

Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.

10.0 out of 10, Exceptional, (1)
"My wife and I decided at the last minute to get away this place fit this it is a closed up ski resort the owner is so nice he actually came out went over everything with us the night we arrived the stay was amazing wood stove was the best we made a pallet on floor by the wood stove was just the best Seymour was the best and did everything to make your stay the best"
Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!
Large, level yard with easy lake access

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (5)
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!
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.