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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (91 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is NZ$1,322
includes taxes & fees
27 Sept - 28 Sept
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, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is NZ$338
includes taxes & fees
24 Sept - 25 Sept
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)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is NZ$328
includes taxes & fees
27 Sept - 28 Sept
Wizard's Roost 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 NZ$328
includes taxes & fees
27 Sept - 28 Sept
SteamPunk Bunk House and Intergalactic Way Station
A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (25 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is NZ$516
includes taxes & fees
24 Sept - 25 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

6. 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 NZ$1,100
includes taxes & fees
28 Sept - 29 Sept
Mohegan Sun Getaway Large Group Retreat
A modern interior with a kitchen, dining area, and living space.

7. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is NZ$1,152
includes taxes & fees
28 Sept - 29 Sept
6 Beds Home w/Game Room Perfect for Groups
A window with a view of a grassy field and trees.

8. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (6 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 NZ$532
includes taxes & fees
27 Sept - 28 Sept
Spacious, unique barn with beautiful views.
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

9. 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.
The price is NZ$1,067
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

10. 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, (9 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 NZ$340
includes taxes & fees
28 Sept - 29 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

11. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (6 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 NZ$410
includes taxes & fees
28 Sept - 29 Sept
Cottage by the Castle – Downtown Spencer
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (23 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
The price is NZ$1,468
includes taxes & fees
27 Sept - 28 Sept
Lake House in Sturbridge w/All the Views!
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
9.6 out of 10, Exceptional, (9 reviews)
"This is a real gem of a find! I loved our stay here. GPS does take you to the back of the building but it’s located next to a large parking lot. Plenty of parking which was great for us because we have an extended cab f350 ford that does not fit into most parking spaces. The other great thing about this house is multiple showers and bathrooms. This is so rare in a CT house. I must’ve searched for hours. The host Pam was super friendly and was so quick to respond. The house was super stocked with...
United States
Jenny
The price is NZ$628
includes taxes & fees
5 Oct - 6 Oct
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

14. 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 NZ$2,984
includes taxes & fees
1 Oct - 2 Oct
Sleeps 15 • Pool • Retreat
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, (20 reviews)
"Perfect location"
United States
Harmony F.
The price is NZ$899
includes taxes & fees
28 Sept - 29 Sept
Spacious 4-bedroom with four and half bathrooms
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

16. 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.
The price is NZ$1,522
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
A bar area with a counter, two green chairs, a refrigerator, and a neon sign.

17. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is NZ$470
includes taxes & fees
24 Sept - 25 Sept
Game Room + Bar Lounge, 35 Min to Boston
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

18. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.4 out of 10, Very good, (6 reviews)
The price is NZ$941
includes taxes & fees
24 Sept - 25 Sept
Clifford Luxury Retreat 3BR Self Check In Home
A spacious kitchen with dark wooden cabinets, a large island with bar stools, and pendant lighting.

19. Luxury Woodland Retreat Game Room Sleeps 6 Near Providence

Luxury Woodland Retreat Game Room Sleeps 6 Near Providence
Scituate
Luxury Woodland Retreat Game Room Sleeps 6 Near Providence
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 & Suites Sturbridge - Brimfield

Comfort Inn & Suites Sturbridge - Brimfield

10/10 Excellent
"Super clean and updated rooms. Friendly staff. Great breakfast, but get there early. Nice area to walk my dogs. Would definitely stay here again."
michele 1-night trip
Posted 11 hours ago
Comfort Inn & Suites Sturbridge - Brimfield

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
220
Accommodation
96 Holiday Homes
Lowest Price
NZ$328
Highest Price
NZ$2,984