A variety of potted flowers and pumpkins on a wooden table in an outdoor setting.

Holiday Homes in Woodstock

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Woodstock holiday homes

A dining area with a high ceiling, skylights, and a view of the outdoors.

1. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (94 reviews)
"Beautiful lake house. The dock with the kayaks and paddle boat made it so much fun for the kids. The dock isnt far from the house but there a decent hill down to it. Totally manageable for most people though. The open house concept kitchen area made it great for everyone to be together."
United States
Amanda S.
The price is AU$910
includes taxes & fees
4 Nov - 5 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (44 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is AU$279
includes taxes & fees
26 Oct - 27 Oct
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

3. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
The price is AU$270
includes taxes & fees
28 Oct - 29 Oct
Wizard's Roost at Underhill Hollow
A room with two wicker chairs and a small round table, a large window, and a red door.

4. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (19 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$270
includes taxes & fees
28 Oct - 29 Oct
SteamPunk Bunk House and Intergalactic Way Station
A modern interior with a kitchen, dining area, and living space.

5. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
10.0 out of 10, Exceptional, (2 reviews)
"Edgar was very responsive and easy to work with. The unit was very clean and well kept. I would definitely stay there again."
United States
debra l.
6 Beds Home w/Game Room Perfect for Groups
A window with a view of a grassy field and trees.

6. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (8 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$434
includes taxes & fees
29 Oct - 30 Oct
Spacious, unique barn with beautiful views.
A round metal fire pit with grilling tools and a red chair in the background.

7. 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
9.2 out of 10, Wonderful, (12 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is AU$304
includes taxes & fees
27 Oct - 28 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A hotel with a central building, outdoor seating area, and a covered patio.

8. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveller
The price is AU$698
includes taxes & fees
2 Nov - 3 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

9. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (40 reviews)
"It was a beautiful property. Well-tended and all the amenities. Loved the view in morning and evening of mountains and sun / moon."
United States
Daniel C.
The price is AU$2,372
includes taxes & fees
25 Oct - 26 Oct
Sleeps 15 • Pool • Retreat
The Cottage is nestled next to the historic Sagendorph Mansion.

10. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AU$370
includes taxes & fees
26 Oct - 27 Oct
Cottage by the Castle – Downtown Spencer
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

11. Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
The price is AU$586
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

12. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
The price is AU$711
includes taxes & fees
25 Oct - 26 Oct
Spacious 4-bedroom with four and half bathrooms
A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

13. 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
9.8 out of 10, Exceptional, (11 reviews)
"Fantastic host. Went out of their way to make our stay very pleasant. Beautiful historic home that felt very welcoming and cozy even though it is so big!"
United States
John
The price is AU$505
includes taxes & fees
2 Nov - 3 Nov
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

14. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.6 out of 10, Excellent, (7 reviews)
The price is AU$751
includes taxes & fees
25 Oct - 26 Oct
Clifford Luxury Retreat 3BR Self Check In Home
A covered deck with outdoor furniture, a grill, and a sliding glass door leading to a bedroom.

15. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is AU$377
includes taxes & fees
25 Oct - 26 Oct
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
A staircase with wooden steps and black balusters, a potted plant on a side table, and a framed floral artwork on the wall.

16. Spacious 5-bedroom home with three full bathrooms in charming Worcester location

Spacious 5-bedroom home with three full bathrooms in charming Worcester location
Worcester
The price is AU$698
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
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

Inn on Storrs

Inn on Storrs

10/10 Excellent
"Everything was perfect. We are looking forward to our next stay."
Mystik 2-night trip
Posted 1 day ago
Inn on Storrs

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
394
Accommodation
96 Holiday Homes
Lowest Price
AU$270
Highest Price
AU$2,372