Woodstock Travel Guide

Tourist 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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock CT
The price is AU$906 per night from 9 Mar to 10 Mar
AU$906
9 Mar - 10 Mar
includes taxes & fees
Stay at this holiday home in Woodstock. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Black Pond and West Woodstock Library are located ...
9.8/10 Exceptional! (81 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 13 Jan 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 AU$877 per night from 9 Mar to 10 Mar
AU$877
9 Mar - 10 Mar
includes taxes & fees
Stay at this beach holiday home in Woodstock. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Roseland Cottage and Taylor Brooke ...
10/10 Exceptional! (22 reviews)
Welcoming host! Beautiful house with great amenities!

Reviewed on 24 Feb 2026

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 Wi-Fi, an in-room coffee maker 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 24 Dec 2025

Get rates
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
See all 309 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 holiday home in Woodstock. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Black Pond and West Woodstock Library are located ...
9.8/10 Exceptional! (81 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 13 Jan 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
Stay at this beach holiday home in Woodstock. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Roseland Cottage and Taylor Brooke ...
10/10 Exceptional! (22 reviews)
Welcoming host! Beautiful house with great amenities!

Reviewed on 24 Feb 2026

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 Wi-Fi, an in-room coffee maker 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 24 Dec 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

Taylor Brooke Winery

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

Taylor Brooke Winery

Roseland Cottage

You can study the exhibits at Roseland Cottage, a museum with a storied past, during your holiday in Woodstock. Visit the lively bars or top-notch restaurants in this family-friendly area.

Roseland Cottage

Roseland Park Golf Course

Enjoy a round of golf in Woodstock at Roseland Park Golf Course. Visit the lively bars or top-notch restaurants in this family-friendly area.

Roseland Park Golf Course

Woodstock Town Beach

Why not spend a lazy afternoon at Woodstock Town Beach during your trip to Woodstock? Take in the festivals while you're in the area.

Woodstock Town Beach

Little River Plaza Shopping Center

You can find the perfect gifts to bring home at Little River Plaza Shopping Center during your visit to South Woodstock. While in this family-friendly area, you can savour the top-notch restaurants.

Little River Plaza Shopping Center

Hauser Preserve

You can take time to visit Hauser Preserve during your travels to Woodstock. Take in the festivals while you're in the area.

Hauser Preserve