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Holiday Homes in Woodstock

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Woodstock holiday homes

Terrace/patio

1. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
United States
Lisa R.
The price is AU$1,017
includes taxes & fees
13 Sept - 14 Sept
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (89 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$1,054
includes taxes & fees
8 Sept - 9 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

3. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (41 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is AU$272
includes taxes & fees
13 Sept - 14 Sept
The Tree House at Underhill Hollow
Exterior

4. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 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 AU$264
includes taxes & fees
11 Sept - 12 Sept
Wizard's Roost at Underhill Hollow
Property grounds

5. 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 AU$264
includes taxes & fees
10 Sept - 11 Sept
SteamPunk Bunk House and Intergalactic Way Station
Interior

6. 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 AU$368
includes taxes & fees
9 Sept - 10 Sept
Spacious, unique barn with beautiful views.
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (24 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 AU$453
includes taxes & fees
9 Sept - 10 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Coffee/tea maker, fridge, microwave, oven

8. 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$819
includes taxes & fees
8 Sept - 9 Sept
Mohegan Sun Getaway Large Group Retreat
Property grounds

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

10. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is AU$890
includes taxes & fees
8 Sept - 9 Sept
6 Beds Home w/Game Room Perfect for Groups
Property grounds

11. 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)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is AU$312
includes taxes & fees
29 Sept - 30 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Property grounds

12. 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 AU$925
includes taxes & fees
4 Oct - 5 Oct
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Exterior

13. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (4 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AU$361
includes taxes & fees
10 Sept - 11 Sept
Cottage by the Castle – Downtown Spencer
TV, fireplace

14. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (38 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$2,204
includes taxes & fees
10 Sept - 11 Sept
Sleeps 15 • Pool • Retreat
2 bedrooms, iron/ironing board, WiFi, bed sheets

15. 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, (8 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 AU$508
includes taxes & fees
15 Sept - 16 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
Coffee/tea maker, fridge, microwave, oven

16. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (18 reviews)
"Perfect location"
United States
Harmony F.
The price is AU$702
includes taxes & fees
9 Sept - 10 Sept
Spacious 4-bedroom with four and half bathrooms
Interior

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is AU$388
includes taxes & fees
15 Sept - 16 Sept
Game Room + Bar Lounge, 35 Min to Boston
3 bedrooms, desk, iron/ironing board, free WiFi

18. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.0 out of 10, Very good, (5 reviews)
The price is AU$749
includes taxes & fees
8 Sept - 9 Sept
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

Inn on Storrs

Inn on Storrs

10/10 Excellent
"I have stayed at four star hotels that did not have with this hotel had this was a diamond in the rough a huge surprise and I will definitely be back my little getaway"
Christine 1-night trip
Posted 15 hours ago
Inn on Storrs

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
4,473
Accommodation
81 Holiday Homes
Lowest Price
AU$116
Highest Price
AU$278