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Upfront pricingWe are not like the others - we include taxes and fees
Our top choices for Woodbury vacation rentals
1. Cozy One Bedroom Apartment Centrally Located in Southbury
Cozy One Bedroom Apartment Centrally Located in SouthburySouthbury
10.0 out of 10, Exceptional, (39 reviews)
"Charles was super responsive and the bed was amazingly comfortable. Also the shower head great water pressure :-)"
Lisbeth
$116 nightly
The price is $131
Dec 1 - Dec 2
Total with taxes and fees
2. Bear Retreat - 2-bedroom house in Waterbury
Bear Retreat - 2-bedroom house in WaterburyWaterbury
10.0 out of 10, Exceptional, (13 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
Radha
$283 nightly
The price is $322
Nov 6 - Nov 7
Total with taxes and fees
3. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!Oakville
$469 nightly
The price is $539
Nov 6 - Nov 7
Total with taxes and fees
4. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!Watertown
9.0 out of 10, Wonderful, (6 reviews)
"In town to visit our new grandchild. It was just my husband and me. It had more then enough room and was very comfortable."
Elizabeth H.
$452 nightly
The price is $515
Nov 6 - Nov 7
Total with taxes and fees
5. The Overlook near South Farms in Litchfield County is Hospitality, integrated.
The Overlook near South Farms in Litchfield County is Hospitality, integrated.Morris
9.8 out of 10, Exceptional, (21 reviews)
"Very clean & cozy with everything we needed!"
Joe K.
$232 nightly
The price is $264
Nov 8 - Nov 9
Total with taxes and fees
6. Private Apartment in Southbury 102
Private Apartment in Southbury 102Southbury
9.2 out of 10, Wonderful, (7 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
Debbie P.
$220 nightly
The price is $250
Nov 17 - Nov 18
Total with taxes and fees
7. Private Apartment in Southbury 101
Private Apartment in Southbury 101Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
Marissa G.
$235 nightly
The price is $267
Dec 6 - Dec 7
Total with taxes and fees
8. Private Apartment in Southbury 104
Private Apartment in Southbury 104Southbury
10.0 out of 10, Exceptional, (1 review)
"Pro Unit very clean, check in was easy and host was responsive to issues 24/7.Unit is large with new appliances in full kitchen.It is located in a beautiful rural area of CT. I highly recommend it"
Daniel R.
$230 nightly
The price is $262
Dec 6 - Dec 7
Total with taxes and fees
9. Cozy private room in a shared home with a Full-size bed and private bathroom.
Cozy private room in a shared home with a Full-size bed and private bathroom.New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
Jim B.
$115 nightly
The price is $130
Nov 9 - Nov 10
Total with taxes and fees
10. Escape to Bantam Lake- With Fireplace and Hot tub!
Escape to Bantam Lake- With Fireplace and Hot tub!Morris
10.0 out of 10, Exceptional, (6 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
Shannon M.
$427 nightly
The price is $486
Nov 18 - Nov 19
Total with taxes and fees
11. Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.Waterbury
8.0 out of 10, Very good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
Dirk N.
$122 nightly
The price is $139
Nov 6 - Nov 7
Total with taxes and fees
12. Cozy Studio apartment in delightful Waterbury with Central Air
Cozy Studio apartment in delightful Waterbury with Central AirWaterbury
2.0 out of 10, (1 review)
"The place wasn’t how the pictures were on the app. It was hard to find the room. The keys for the room are very hard to open the room door . It’s like you have to struggle just to get inside . The room is inside of an abandoned building… some staff in the building was telling me that I shouldn’t be staying there or they wouldn’t stay there so it made me feel unsafe… the bed doesn’t match the head board. Everything just doesn’t match the images the host posted.."
zynaisha
$89 nightly
The price is $101
Dec 2 - Dec 3
Total with taxes and fees
13. The Jefferson Guest House, Spacious, Special Views
The Jefferson Guest House, Spacious, Special ViewsLitchfield
10.0 out of 10, Exceptional, (9 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
Jennifer A.
$361 nightly
The price is $361
Nov 8 - Nov 9
Total with taxes and fees
14. Las Flores Villa
Las Flores VillaNew Preston
10.0 out of 10, Exceptional, (1 review)
$1,343 nightly
The price is $1,544
Nov 6 - Nov 7
Total with taxes and fees
15. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & DiningNew Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
Jeni O.
$718 nightly
The price is $819
Dec 1 - Dec 2
Total with taxes and fees
16. 1-bedroom vacation home 22 minutes from Quinnipiac University
1-bedroom vacation home 22 minutes from Quinnipiac UniversityWolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
David G.
$337 nightly
The price is $384
Nov 30 - Dec 1
Total with taxes and fees
17. Private Apartment in Southbury 105
Private Apartment in Southbury 105Southbury
$230 nightly
The price is $262
Nov 9 - Nov 10
Total with taxes and fees
18. The Little Lake Cabin with hot tub
The Little Lake Cabin with hot tubNew Fairfield
10.0 out of 10, Exceptional, (6 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
Lyndsey F.
$462 nightly
The price is $527
Nov 8 - Nov 9
Total with taxes and fees
19. 1 King Bed | Non-Smoking
1 King Bed | Non-SmokingBethel
10.0 out of 10, Exceptional, (3 reviews)
"We found plenty of space for our small group plus pets. Loved having a private bathroom,it made mornings smooth."
Anonymous traveler
$114 nightly
The price is $131
Nov 23 - Nov 24
Total with taxes and fees
20. 191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospital
191 Seymour, Ave. Derby · Spacious Renovated 3 bedroom near GriffinHospitalDerby
8.6 out of 10, Excellent, (8 reviews)
"Great stay! Perfect location for my needs. Clean and inviting rental. Modern and well kept. Will stay again. "
Bary B.
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.
Top Woodbury Hotel Reviews
The Milestone Inn
The Milestone InnWoodbury
10/10 Excellent
It was so quaint and charming! The room was very clean and generously sized, as was the bed. The fridge and microwave were nice added conveniences. Parking was extremely convenient. Check in was over the phone, which was incredibly easy and quick. I loved everything about the Milestone Inn and look forward to staying there again!
Elin
