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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Rupert cottages

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

1. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Perfect little stay. Best parts of being out in the middle of the woods that also has great cell service. Everything you'd need to enjoy a couple days out in "
United States
Victor L.
$170 nightly
The price is $189
Oct 25 - Oct 26
Total with taxes and fees
Peaceful Cottage Retreat
A row of white houses with a clear night sky and visible stars.

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.
$349 nightly
The price is $391
Oct 25 - Oct 26
Total with taxes and fees
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.
$432 nightly
The price is $479
Oct 25 - Oct 26
Total with taxes and fees
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
$550 nightly
The price is $622
Oct 25 - Oct 26
Total with taxes and fees
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

The Manchester View

The Manchester View

10/10 Excellent
"Great place and clean..Uber is not available fyi"
nicholas 1-night trip
Posted 3 hours ago
The Manchester View

Find out more about Rupert

Rupert Cottages information

Number of reviews
100
Accommodation
85 Cottages
Lowest Price
$189
Highest Price
$622

Frequently asked questions

Why book your cottage in Rupert with Expedia?
Reserving a cottage in Rupert is as simple as entering your travel dates and selecting an ideal place for a getaway in the outdoors. From ritzy retreats to budget-friendly stays and cottages that come with amenities like laundry facilities, Expedia has something for all tastes and styles. As for the best deals around? We have them too!
How can I find cheap cottages in Rupert?
With Expedia's helpful filter tool, comparing cheap cottages in Rupert is easy. To find stays that'll make your hip pocket happy, tailor your search results by star rating, budget and amenities.
What is there to do in Rupert near my cottage?
The best travel accessory is a well-thought-out travel plan. Merck Forest Farmland Center is a top place to kick off your exploration of Rupert.

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