Search Vacation Homes in Woodbury

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Woodbury

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

9.0 out of 10, Wonderful, (17)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"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

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is AED 826
AED 1,188 total
includes taxes & fees
4 Aug - 5 Aug
Tranquil Litchfield Connecticut Retreat".

Private Annex/Former Artist Studio

10.0 out of 10, Exceptional, (51)
"Great property great location wonderful day"
Private Annex/Former Artist Studio

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

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

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (122)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very Good, (3)
"Great spot and location, house was clean and enjoyable. Pool needs additional care and cleaning "
Spacious Woodbury Home w/ Pool + Hot Tub!

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

10.0 out of 10, Exceptional, (57)
"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 AED 1,062
AED 1,802 total
includes taxes & fees
5 Aug - 6 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (4)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (1)
"The property was great and the house was huge even for all 12 of us "
The price is AED 542
AED 2,555 total
includes taxes & fees
5 Aug - 6 Aug
CT Gate House Goshen CT, Gate House Goshen CT

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (28)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown

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

10.0 out of 10, Exceptional, (9)
"We had a wonderful vacation with our grandchildren and family. The children lived in the water if not kayaking or water boards they were fishing!! Rainy days puzzles were our entertainment the summer house provided everything one wanted or needed. It was a very delightful vacation"
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

Litchfield County Getaway

10.0 out of 10, Exceptional, (44)
"Property is a great getaway from a fast paced life. Quiet and beautiful. Open floor concept. Country living with all the update of the city. Very clean. "
Litchfield County Getaway

Private hidden gem walking distance to town, restaurants, and shopping!

9.8 out of 10, Exceptional, (18)
"Great property!"
Private hidden gem walking distance to town, restaurants, and shopping!

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (12)
"The house was as advertised and located in a really quiet neighborhood. The host was easy to work with and responded to me each time I texted her. If the opportunity ever comes up again, we would definitely stay at this property again."
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

2.0 star property
10.0 out of 10, Exceptional, (7)
"We met our kids (who live on the east coast) at Natures Nest and really enjoyed our time here. We cooked 2 big meals and the kitchen had everything we needed…even spices & coffee. And Marco left some apples, sweets and wine for us! He was very responsive and helpful anytime we had questions, and gave us great recommendations. Everything was great!"
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

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

10.0 out of 10, Exceptional, (3)
"Home was very nice and as described. Perfect for our needs "
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

Make lifelong memories at this New England Quintessential Country Getaway

10.0 out of 10, Exceptional, (41)
"We headed back to my hometown just surprise my parents with a visit from their grandchildren and great grandchildren."
Make lifelong memories at this New England Quintessential Country Getaway

Awesome Lake Home with tons of fun!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot "
The price is AED 1,653
AED 2,850 total
includes taxes & fees
5 Aug - 6 Aug
Awesome Lake Home with tons of fun!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Woodbury Hotel Reviews