Top Guest Houses in Town of Chesterfield in 2026

A stone bridge over a river with a waterfall and a small building on the right.

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Our top choices for Town of Chesterfield guest houses

A room with two beds, a wooden dresser, a small table, and a rug with a bear design.

1. RoosterComb Inn

Keene Valley

Sharon

AED 436 total

includes taxes & fees

15 Oct - 16 Oct

A living room with two purple sofas, a fireplace, and a table with a floral tablecloth.

2. The Old Lantern Inn and Barn

Charlotte

Michelle

A two-story house with a porch and a separate red building.

3. The Birch & Berry Inn

Hinesburg

Morgan

AED 574 total

includes taxes & fees

18 Oct - 19 Oct

A patio area with two chairs, a fire pit, and a view of the water.

4. Valcour Inn & Boathouse

Peru

Shengle

AED 716 total

includes taxes & fees

2 Nov - 3 Nov

A patio area with wooden furniture, a striped umbrella, and potted plants.

5. 254 South Union Street Guest House

South End

Alan

AED 1,117 total

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with a dining area, a staircase, and a view of the outdoors.

6. Relaxing spa-like tiny house w/ hot tub, sauna, beach access, dog-friendly

Malletts Bay

Jennifer

AED 1,560 total

includes taxes & fees

20 Oct - 21 Oct

A porch with white columns, a bench, and potted geraniums in red, pink, and orange.

7. Williston Village Inn

Williston North

"Honestly, after a number of disappointing stays recently, we weren't expecting much so we could avoid being disappointed. But, we were anything but. We were in the maple room, which had private access to outside, a nice living room, a small kitchen (no stove), a large bedroom and very comfortable bed, and a semi small bathroom that was laid out well. Loved there was a personal shower head. Everything was clean and well maintained. We were very impressed and happy with our stay. The lady who...

Jason

A stone staircase leading up a hill with white Adirondack chairs at the top.

8. South Hero Guesthouse with lake access and great sunsets

South Hero

william r.

A bedroom with a sloped ceiling, wooden walls, a bed with a striped blanket, and a tapestry on the wall.

9. Bright and Cozy Prvt Treehouse Apt Near downtown!

Old North End

Charles

AED 1,312 total

includes taxes & fees

26 Oct - 27 Oct

A rustic outdoor setting with a pond, wooden structures, and a building in the background.

10. A secluded getaway in a great location - 30 minutes from Lake Placid!

Elizabethtown

Emily A.

AED 772 total

includes taxes & fees

20 Oct - 21 Oct

A wooden interior with a kitchen area, two stools, and a patterned rug.

11. River Rock Chalet, in-law suite with private entrance, 2 bedrooms and 2 baths.

Jay

Cory G.

A cabin with a porch, a covered deck, and a dirt path leading to it.

12. The Loft - Keene | Modernized Private Guesthouse in Town | Centrally Located to Major Trailheads

Keene

"Our stay at the Loft was perfect. We were looking for a place to stay while we climbed the high peaks for a few days, and we couldn’t have made a better choice. The Loft had everything we could have needed, tucked into a quiet and private location. The house was immaculate and so well designed for the space. The amenities were thoughtful and of quality. The location was also perfect, just a few steps away from a wonderful restaurant and no more than 20 minutes from other high peaks neighborhoods...

Julie B.

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Top Town of Chesterfield Hotel Reviews

Laurel Lake Placid

10/10 Excellent

"Great location! Excellent for a family vacation. Walking distance to shops, restaurants, Olympic museum. Steps from Mirror Lake. The only issue was the parking. This was a busy weekend and there were not enough parking spots. Apart from that, it was great!"