A rural landscape with a barn on a hill, surrounded by autumn-colored trees.

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Rupert cottages

A house with a gravel driveway, surrounded by trees and a well-maintained lawn.

1. A peaceful retreat in a cabin

A peaceful retreat in a cabin
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
The price is AED 459
AED 636 total
includes taxes & fees
16 Dec - 17 Dec
A peaceful retreat in a cabin
A white building with green shutters and a small porch, surrounded by autumn foliage and a clear sky.

2. Comfy Cottage with Private Hot Tub in Historic East Poultney

Comfy Cottage with Private Hot Tub in Historic East Poultney
Poultney
10.0 out of 10, Exceptional, (18 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is AED 826
AED 1,407 total
includes taxes & fees
16 Nov - 17 Nov
Comfy Cottage with Private Hot Tub in Historic East Poultney
A wooden deck with a view of a lake surrounded by trees.

3. Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Fort Ann
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is AED 1,298
AED 1,559 total
includes taxes & fees
16 Nov - 17 Nov
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Terrace/patio

4. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
The price is AED 2,158
AED 2,651 total
includes taxes & fees
16 Nov - 17 Nov
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
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 Rupert Hotel Reviews

Toll Road Inn

Toll Road Inn

10/10 Excellent
"Toll Road Inn is so charming and comfortable. The room was spotless, and the decor was perfectly retro. We really appreciated the little snacks as well. The lobby is cozy (with 24 hour coffee/tea and non-dairy milk- thank you!) the brook out back with Adirondack chairs is delightful. We will definitely stay again!"
Barbara 2-night trip
Posted 2 days ago
Toll Road Inn

Frequently asked questions

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