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Our top choices for Woodstock holiday homes

1. Secluded 2-Acre Lakefront Home! Book Your Getaway!
Secluded 2-Acre Lakefront Home! Book Your Getaway!Woodstock
9.8 out of 10, Exceptional, (95 reviews)
The price is NZ$1,078
includes taxes & fees
8 Nov - 9 Nov

2. The Tree House at Underhill Hollow
The Tree House at Underhill HollowThompson
9.4 out of 10, Exceptional, (46 reviews)
The price is NZ$321
includes taxes & fees
9 Nov - 10 Nov

3. Wizard's Roost at Underhill Hollow
Wizard's Roost at Underhill HollowNorth Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
The price is NZ$311
includes taxes & fees
9 Nov - 10 Nov

4. SteamPunk Bunk House and Intergalactic Way Station
SteamPunk Bunk House and Intergalactic Way StationThompson
10.0 out of 10, Exceptional, (20 reviews)
The price is NZ$322
includes taxes & fees
8 Nov - 9 Nov

5. Spacious, unique barn with beautiful views.
Spacious, unique barn with beautiful views.Hampton
10.0 out of 10, Exceptional, (11 reviews)
The price is NZ$520
includes taxes & fees
10 Nov - 11 Nov

6. 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)
The price is NZ$811
includes taxes & fees
9 Nov - 10 Nov

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 8Brimfield
9.2 out of 10, Wonderful, (12 reviews)
The price is NZ$383
includes taxes & fees
15 Nov - 16 Nov

8. Lake House in Sturbridge w/All the Views!
Lake House in Sturbridge w/All the Views!Sturbridge
9.6 out of 10, Exceptional, (25 reviews)
The price is NZ$1,428
includes taxes & fees
11 Nov - 12 Nov

9. Sleeps 15 • Pool • Retreat
Sleeps 15 • Pool • RetreatBrimfield
10.0 out of 10, Exceptional, (40 reviews)
The price is NZ$3,031
includes taxes & fees
9 Nov - 10 Nov

10. Cottage by the Castle – Downtown Spencer
Cottage by the Castle – Downtown SpencerSpencer
10.0 out of 10, Exceptional, (9 reviews)
The price is NZ$397
includes taxes & fees
8 Nov - 9 Nov

11. Spacious 4-bedroom with four and half bathrooms
Spacious 4-bedroom with four and half bathroomsWorcester
9.8 out of 10, Exceptional, (23 reviews)
The price is NZ$855
includes taxes & fees
8 Nov - 9 Nov

12. Clifford Luxury Retreat 3BR Self Check In Home
Clifford Luxury Retreat 3BR Self Check In HomeNorthbridge
8.6 out of 10, Excellent, (7 reviews)
The price is NZ$775
includes taxes & fees
9 Nov - 10 Nov

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 RestaurantsSomers
9.8 out of 10, Exceptional, (12 reviews)
The price is NZ$611
includes taxes & fees
17 Nov - 18 Nov

14. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to BostonWorcester
8.0 out of 10, Very good, (1 review)
The price is NZ$601
includes taxes & fees
13 Nov - 14 Nov
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.
Learn more about Woodstock
Explore the historic Roseland Cottage with its vibrant gardens and Gothic Revival architecture that tells stories of New England's past. Spend afternoons sampling local vintages at Taylor Brooke Winery or enjoying a round at Woodstock Golf Course when the morning light illuminates the rolling fairways.

























































