Woodstock Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Woodstock

The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (821 reviews)
Wonderful place to stay
"We love Woodstock and this was out first time staying here at The Shire. The staff was very friendly, and the room was fun and clean, and oh what a view!"

Reviewed on 14 Sept, 2025

Get rates
The Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is S$901 per night from 21 Sept to 22 Sept
S$901
21 Sept - 22 Sept
includes taxes & fees
9.2/10 Wonderful! (533 reviews)
Old world charm
"What a wonderful inn. Same class as The Greenbrier and The Homestead. Old world charm."

Reviewed on 12 Sept, 2025

Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
9.2/10 Wonderful! (1,001 reviews)
"Property was nice; room had some wear and tear...lower level a distinct odor of chlorine (pool); couldn't get our safe fixed while we were there and we were a bit put off by no phones in the rooms..other than that very nice... the paying extra for amenities, why not just include it in the room rate? ..."

Reviewed on 10 Sept, 2025

Get rates
On The River Inn
See all 2,611 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

Saskadena Six Ski Area

Hit the slopes in Woodstock with a visit to Saskadena Six Ski Area. Wander the riverfront in this quaint area.

Saskadena Six Ski Area

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.