Holiday Homes in Woodstock

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 June - 28 June
In three months
24 July - 26 July
In four months
21 Aug - 23 Aug

Our top choices for Woodstock holiday homes

Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (23 reviews)
"Great property"
United States
gary b.
The price is AU$1,022
includes taxes & fees
4 May - 5 May
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (84 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AU$1,057
includes taxes & fees
4 May - 5 May
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$264
includes taxes & fees
3 May - 4 May
SteamPunk Bunk House and Intergalactic Way Station
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is AU$264
includes taxes & fees
4 May - 5 May
Wizard's Roost at Underhill Hollow
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.2 out of 10, Wonderful, (35 reviews)
"Such a fun getaway!"
United States
Patrice D.
The price is AU$272
includes taxes & fees
4 May - 5 May
The Tree House at Underhill Hollow
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is AU$369
includes taxes & fees
5 May - 6 May
Spacious, unique barn with beautiful views.
Books

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
8.0 out of 10, Very good, (2 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is AU$307
includes taxes & fees
3 May - 4 May
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (10 reviews)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
United States
Deb H.
The price is AU$707
includes taxes & fees
4 May - 5 May
Spacious 4-bedroom with four and half bathrooms
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
The price is AU$448
includes taxes & fees
3 May - 4 May
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Interior

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (38 reviews)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is AU$400
includes taxes & fees
27 May - 28 May
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
TV, fireplace

Sleeps 15 • Pool • World Cup 2026 • Retreat

Sleeps 15 • Pool • World Cup 2026 • Retreat
Brimfield
10.0 out of 10, Exceptional, (33 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is AU$2,339
includes taxes & fees
1 June - 2 June
Sleeps 15 • Pool • World Cup 2026 • Retreat
Outdoor dining

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.4 out of 10, Exceptional, (20 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is AU$463
includes taxes & fees
17 May - 18 May
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
2 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Somers
The price is AU$480
includes taxes & fees
17 May - 18 May
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Property grounds

Leicester Lake Front Home, Come Relax!

Leicester Lake Front Home, Come Relax!
Leicester
10.0 out of 10, Exceptional, (34 reviews)
"We loved our stay over Christmas at this beautiful Leicester home. It was spacious, had everything we needed, and the view was spectacular. The host, Lucas, was very responsive and accessible for anything we needed during our stay. We will definitely book again when in the area visiting family. "
United States
Kristin G.
Leicester Lake Front Home, Come Relax!
Fridge, microwave, stovetop, coffee/tea maker

Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
The price is AU$992
includes taxes & fees
5 May - 6 May
Mohegan Sun Getaway Large Group Retreat
Interior

Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
The price is AU$570
includes taxes & fees
3 May - 4 May
Cozy 3-bedroom house in serene Worcester with fitness room and office
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is AU$1,120
includes taxes & fees
13 May - 14 May
6 Beds Home w/Game Room Perfect for Groups
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (20 reviews)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is AU$1,298
includes taxes & fees
3 May - 4 May
Lake House in Sturbridge w/All the Views!
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.
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Top Woodstock Hotel Reviews

Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

6/10 Okay
"Property was clean, parking was included which was nice, rooms where clean as well. Check in took a while though, had to wait in line for a good 15-20 minutes because only 1 person was running the front desk."
Carlotta 1-night trip
Posted 2 hours ago
Comfort Inn Auburn - Worcester

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
341
Accommodation
96 Holiday Homes
Lowest Price
AU$264
Highest Price
AU$2,339