Woodstock

Travel Guide

Chrysanthemums and pumpkins for sale at a farm stand near Woodstock, Connecticut.
Chrysanthemums and pumpkins for sale at a farm stand near Woodstock, Connecticut.
Sunrise over farmland near South Woodstock, Connecticut.
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock CT
The price is CA $376 per night from Feb 20 to Feb 21
CA $376
CA $704 total
Feb 20 - Feb 21
includes taxes & fees
Stay at this vacation home in Woodstock. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Black Pond and Campert Preserve are located ...
9.8/10 Exceptional! (80 reviews)
We had a great stay! Clean and very comfortable. The big kitchen was equipped with everything you’d need and had a big table for hosting the whole family.

Reviewed on Jan 13, 2026

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock CT
The price is CA $338 per night from Feb 22 to Feb 23
CA $338
CA $656 total
Feb 22 - Feb 23
includes taxes & fees
Book a stay at this beach vacation home in Woodstock. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Roseland Cottage and Taylor ...
10/10 Exceptional! (21 reviews)
Great property

Reviewed on Dec 2, 2025

Stunning Lakefront Escape! Book Your Dream Getaway!
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
The price is CA $147 per night from Feb 9 to Feb 10
CA $147
CA $164 total
Feb 9 - Feb 10
includes taxes & fees
Book a stay at this business-friendly hotel in Southbridge. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,409 reviews)
Staff was great room was very clean

Reviewed on Jan 31, 2026

Wellsworth Hotel
See all 305 properties in Woodstock
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.
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock CT
Stay at this vacation home in Woodstock. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Black Pond and Campert Preserve are located ...
9.8/10 Exceptional! (80 reviews)
We had a great stay! Clean and very comfortable. The big kitchen was equipped with everything you’d need and had a big table for hosting the whole family.

Reviewed on Jan 13, 2026

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock CT
Book a stay at this beach vacation home in Woodstock. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Roseland Cottage and Taylor ...
10/10 Exceptional! (21 reviews)
Great property

Reviewed on Dec 2, 2025

Stunning Lakefront Escape! Book Your Dream Getaway!
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn

Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn

Woodstock CT
Stay at this apartment in Woodstock. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions May Memorial Library and North Woodstock ...
10/10 Exceptional! (13 reviews)
An amazing place,surrounded by pines,Clean and comfy.

Reviewed on Dec 24, 2025

Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
See all properties in Woodstock
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.

Popular places to visit

Goodell Morse Memorial Forest

You can take time to visit Goodell Morse Memorial Forest during your travels to Woodstock. Take in the festivals while you're in the area.

Goodell Morse Memorial Forest

Roseland Cottage

You can study the exhibits at Roseland Cottage, a museum with a storied past, during your travels to Woodstock. Check out the top-notch restaurants or lively bars in this quaint area.

Roseland Cottage

Taylor Brooke Winery

You can enjoy a tasting or tour at Taylor Brooke Winery during your travels to Woodstock. While in this quaint area, you can savor the top-notch restaurants.

Taylor Brooke Winery

Woodstock Golf Course

Enjoy a round of golf in Woodstock at Woodstock Golf Course. Check out the lively bars or top-notch restaurants in this quaint area.

Woodstock Golf Course

West Woodstock Library

West Woodstock Library is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Take in the festivals while you're in the area.

West Woodstock Library

Black Pond

Commune with nature and explore the great outdoors at Black Pond during your travels in Woodstock. Take in the festivals while you're in the area.

Black Pond