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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Rupert cottages

A single-story house with a gabled roof, large windows, and a chimney.

1. Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (60 reviews)
"The cottage is in a nice spot on the lake. It is accurately depicted in the listing and was great for our trip"
United States
Jim V.
The price is €386
includes taxes & fees
9 Oct - 10 Oct
Quaint, friendly cottage with lakefront location & water views
A house with a gravel driveway, surrounded by trees and a well-maintained lawn.

2. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (49 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
The price is €171
includes taxes & fees
1 Oct - 2 Oct
Peaceful Cottage Retreat
A row of white houses with a clear night sky and visible stars.

3. 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, (16 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is €337
includes taxes & fees
14 Oct - 15 Oct
Comfy Cottage with Private Hot Tub in Historic East Poultney
A wooden deck with picnic tables and chairs, surrounded by dense trees and a clear sky.

4. Hilltop Cottage

Hilltop Cottage
Argyle
10.0 out of 10, Exceptional, (3 reviews)
"great place to stay"
United States
Anna Z.
The price is €769
includes taxes & fees
30 Sept - 1 Oct
Hilltop Cottage
A wooden deck with a view of a lake surrounded by trees.

5. 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, (31 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is €318
includes taxes & fees
5 Oct - 6 Oct
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Exterior

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

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
The price is €469
includes taxes & fees
30 Sept - 1 Oct
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
"We really enjoyed our stay at The Manchester View. Our terrace room was spacious and comfortable, and the view was absolutely to die for—definitely one of the highlights of our stay. Check-in and checkout were both very easy, and the included breakfast was a nice touch and a great way to start the day. The location is also very convenient, especially for visiting Hildene, which is nearby and was a very special place and one of the highlights of our trip. A comfortable, relaxing stay with beautiful Vermont views. We would definitely stay here again."
Jose 1-night trip
Posted 4 hours ago
The Manchester View

Find out more about Rupert

Rupert Cottages information

Number of reviews
159
Accommodation
88 Cottages
Lowest Price
€171
Highest Price
€769

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 Centre is a top place to kick off your exploration of Rupert.