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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is €586
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. 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 €173
includes taxes & fees
18 Oct - 19 Oct
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

3. 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 €178
includes taxes & fees
15 Oct - 16 Oct
The Tree House at Underhill Hollow
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

4. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €173
includes taxes & fees
15 Oct - 16 Oct
SteamPunk Bunk House and Intergalactic Way Station
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

5. Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A modern interior with a kitchen, dining area, and living space.

6. 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, (1 review)
6 Beds Home w/Game Room Perfect for Groups
A window with a view of a grassy field and trees.

7. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 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 €277
includes taxes & fees
16 Oct - 17 Oct
Spacious, unique barn with beautiful views.
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

8. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

9. 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, (10 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 €206
includes taxes & fees
3 Nov - 4 Nov
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.

10. 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 €494
includes taxes & fees
2 Nov - 3 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

11. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 reviews)
"Pictures don't do this house justice! Great communication from start to finish, very clean house & property, coolest house we've ever stayed at. Hope to stay again!"
United States
Mike T.
The price is €749
includes taxes & fees
18 Oct - 19 Oct
Lake House in Sturbridge w/All the Views!
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

12. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (39 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 €1,568
includes taxes & fees
18 Oct - 19 Oct
Sleeps 15 • Pool • Retreat
The Cottage is nestled next to the historic Sagendorph Mansion.

13. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is €216
includes taxes & fees
18 Oct - 19 Oct
Cottage by the Castle – Downtown Spencer
A stone wall, a metal gate, and a building with a blue door and a number '74' sign.

14. A Timeless Retreat at Historic Crompton House

A Timeless Retreat at Historic Crompton House
Elm Park
10.0 out of 10, Exceptional, (1 review)
"This is a beautiful property! Great location and amazing hosts! We had everything we needed and were very comfortable. I highly recommend this place!"
United States
Jessica H.
A Timeless Retreat at Historic Crompton House
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

15. 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)
"Very clean and readily met the needs of our family of 7 traveling on vacation from Washington DC to Maine. Would stay again."
United States
Jim O.
The price is €452
includes taxes & fees
15 Oct - 16 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.

16. 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 €330
includes taxes & fees
27 Oct - 28 Oct
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

17. 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 €401
includes taxes & fees
31 Oct - 1 Nov
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

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

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
The price is €239
includes taxes & fees
15 Oct - 16 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.

19. 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 €447
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom home with three full bathrooms in charming Worcester location
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

20. 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 €477
includes taxes & fees
18 Oct - 19 Oct
Clifford Luxury Retreat 3BR Self Check In Home
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"1"
Claire 1-night trip
Posted 4 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
418
Accommodation
98 Holiday Homes
Lowest Price
€173
Highest Price
€1,568