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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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)
"Great experience. Thank you "
United States
edmund d.
The price is NZ$1,239
includes taxes & fees
11 Aug - 12 Aug
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, (87 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$1,340
includes taxes & fees
1 Sept - 2 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

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

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is NZ$447
includes taxes & fees
18 Aug - 19 Aug
Game Room + Bar Lounge, 35 Min to Boston
Interior

4. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is NZ$329
includes taxes & fees
10 Aug - 11 Aug
The Tree House at Underhill Hollow
Exterior

5. 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 NZ$319
includes taxes & fees
10 Aug - 11 Aug
Wizard's Roost at Underhill Hollow
Property grounds

6. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is NZ$319
includes taxes & fees
17 Aug - 18 Aug
SteamPunk Bunk House and Intergalactic Way Station
Exterior detail

7. Quintessential New England Home w/ Patio & Grill!

Quintessential New England Home w/ Patio & Grill!
Putnam
10.0 out of 10, Exceptional, (8 reviews)
"A perfect place to bring our family together to celebrate our parents’ 50th anniversary! The house had everything we needed, was beautifully decorated and thoughtfully furnished, and felt warm and welcoming from the moment we arrived. A truly special stay."
United States
Laurie and Dan C.
Quintessential New England Home w/ Patio & Grill!
Interior

8. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (5 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$449
includes taxes & fees
12 Aug - 13 Aug
Spacious, unique barn with beautiful views.
TV

9. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is NZ$1,171
includes taxes & fees
10 Aug - 11 Aug
6 Beds Home w/Game Room Perfect for Groups
Coffee/tea maker, fridge, microwave, oven

10. 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$1,166
includes taxes & fees
10 Aug - 11 Aug
Mohegan Sun Getaway Large Group Retreat
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (22 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 NZ$637
includes taxes & fees
18 Aug - 19 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Property grounds

12. 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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is NZ$333
includes taxes & fees
11 Aug - 12 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior

13. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is NZ$398
includes taxes & fees
10 Aug - 11 Aug
Cottage by the Castle – Downtown Spencer
Interior

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (22 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$1,532
includes taxes & fees
3 Sept - 4 Sept
Lake House in Sturbridge w/All the Views!
TV, fireplace

15. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (37 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 NZ$2,687
includes taxes & fees
31 Aug - 1 Sept
Sleeps 15 • Pool • Retreat
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, (16 reviews)
"Perfect location"
United States
Harmony F.
The price is NZ$858
includes taxes & fees
23 Aug - 24 Aug
Spacious 4-bedroom with four and half bathrooms
3 bedrooms, desk, iron/ironing board, free WiFi

17. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
9.0 out of 10, Wonderful, (2 reviews)
"We loved our stay here. The home and the host were both exceptional. We highly recommend this home!"
United States
Martin G.
The price is NZ$920
includes taxes & fees
11 Aug - 12 Aug
Clifford Luxury Retreat 3BR Self Check In Home
2 bedrooms, iron/ironing board, WiFi, bed sheets

18. 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, (7 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$600
includes taxes & fees
8 Sept - 9 Sept
Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants
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

Sturbridge Plaza Hotel

Sturbridge Plaza Hotel

8/10 Good
"NA"
Andrew 1-night trip
Posted 13 hours ago
Sturbridge Plaza Hotel

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
279
Accommodation
95 Holiday Homes
Lowest Price
NZ$319
Highest Price
NZ$2,687