Woodstock Holiday Homes from €165: Search Top House Rentals

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Our top choices for Woodstock holiday homes

A deck with outdoor furniture overlooking a lake, surrounded by trees.

1. Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock

"We loved the house and the grounds looking over the lake. The house was very clean and had everything we needed. The yard, front and back were really lovely. The backyard overlooked Quasset Lake. We were fortunate to enjoy pleasant weather. The beds were comfortable. The living room and kitchen overlooked the lake with a large deck off the area. There is shade available over the deck if the sun gets too hot. We were there only for the weekend, but had a fabulous time."

Gayle B.

includes taxes & fees

30 Aug - 31 Aug

A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Woodstock

Emma S.

includes taxes & fees

3 Sept - 4 Sept

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

Thompson

Douglas C.

includes taxes & fees

31 Aug - 1 Sept

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

Thompson

Pauline S.

includes taxes & fees

30 Aug - 31 Aug

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

5. Wizard's Roost at Underhill Hollow

North Grosvenordale

Mateo A.

includes taxes & fees

30 Aug - 31 Aug

A window with a view of a grassy field and trees.

6. Spacious, unique barn with beautiful views.

Hampton

Kevan W.

includes taxes & fees

31 Aug - 1 Sept

A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

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

Ashford

Jason C.

includes taxes & fees

3 Sept - 4 Sept

A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

8. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Brimfield

Pamela L.

includes taxes & fees

31 Aug - 1 Sept

A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

9. Sleeps 15 • Pool • Retreat

Brimfield

Daniel C.

includes taxes & fees

31 Aug - 1 Sept

10. Cottage by the Castle – Downtown Spencer

Spencer

Sarah S.

includes taxes & fees

31 Aug - 1 Sept

A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

11. Spacious 4-bedroom with four and half bathrooms

Worcester

Harmony F.

includes taxes & fees

22 Sept - 23 Sept

A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

12. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Somers

"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...

Jenny

includes taxes & fees

1 Sept - 2 Sept