Rupert occupies a beautiful spot in Bennington County, known for its rustic landscapes and fruit orchards. There are many vacation rentals in the area, such as farmhouses set in picturesque locations in the Green Mountains area. A stay at Rupert will give you opportunities to get closely acquainted with nature, taste some wonderful local cuisine, and enjoy activities like golfing and fishing.

Choose the perfect vacation rental
Best Vacation Home Deals in Rupert
Save up to 52%
Book the ideal vacation home for as little as $176 per night by searching among the 15 options available in Rupert. Every one of the vacation rentals from our partner websites are directly compared by the search engine , allowing you to save up to 58%.
Top-Rated Rentals and Accommodations in Rupert
Book Vacation Rental Offers with the Highest User Rating
Recommended Vacation Rentals in Rupert
Find your perfect vacation rental in Rupert: from $176 per night
Budget-friendly Vacation Rentals in Rupert
Find Fantastic yet Inexpensive Offers
Dog-Friendly Vacation Rentals
Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Rupert!
Best vacation rentals with a balcony
Looking for a home with a balcony? Check out these vacation homes in Rupert with their own private patios and balconies.
Apartments With Balconies or Patios
Looking for a home with a balcony? Check out these vacation homes in Rupert with their own private patios and balconies.
Popular Rental Amenities in Rupert
Use filters to search and find an offer matching your requirements among all of the properties in Rupert. In Rupert, 5 properties include "Pets allowed". So, if you are looking for a pet-friendly rental, use the Pets allowed filter to compare these rentals. Not as many accommodations in Rupert are available if you dislike handwashing dishes or if you don't have a dog as "No pets allowed" and "Dishwasher" are not often provided in Rupert.
The Weather in Rupert
Check out our climate diagram to find the perfect month for your vacation. The highest average temperatures are in the month of July. Conversely, January is the coolest month in Rupert, with temperatures going under 12° The rainiest month is December while the driest month is August.
7-Day Weather Forecast in Rupert
Accommodations for your vacation in Rupert
Information about vacation rentals in Rupert
💳 Possible discounts | up to 58% |
---|---|
🌙 Nightly prices starting at | $176 |
⭐ Popular amenities | Pets allowed, Pool and Fireplace |
🐾 Pet friendly homes | 4 homes |
🏊 Vacation rentals with pools | 4 homes |
Frequently Asked Questions
What is the average price per night for a vacation home in Rupert?
The nightly price of accommodations in Rupert starts at $176. If you’re interested in a house rental, the average price is $706 per night. A villa Rupert will cost $1,002 per night on average.
How many vacation rentals are available for booking in Rupert?
There are currently 15 vacation rentals available for booking for your next trip.
What are the most popular amenities for vacation rentals in Rupert?
Three most popular amenities for vacation rentals in Rupert include accommodations with: Pets allowed, Pool, and Fireplace.
How many vacation homes with pools are there in Rupert?
There are 4 vacation rentals from 5 providers in Rupert.
Are dogs allowed in vacation rentals in Rupert?
If you are traveling with a pet in Rupert - 44% of rentals allow pets.
What's the best time of year to travel to Rupert?
If looking for a vacation rental in Rupert, consider that rainy season is typically in December or January, with August often being the driest.
We list offers from thousands of providers, including











Vacation Destinations Near Rupert
-
Manchester, VT Vacation Rentals
-
Stratton Mountain Vacation Rentals
-
Ludlow Vacation Rentals
-
Dover Vacation Rentals
-
Diamond Point Vacation Rentals
-
Vacation Rentals in Lake George, NY
-
Wilmington Vacation Rentals
-
Saratoga Springs Vacation Rentals
-
Vacation Rentals in Killington, VT
-
Woodstock Vacation Rentals
-
Chestertown Vacation Rentals
-
Vacation Rentals in the Adirondacks, NY
-
Schroon Lake Vacation Rentals
-
Cheshire Vacation Rentals
-
Accommodation in Albany
-
North Chatham Vacation Rentals
-
Gloversville Vacation Rentals
-
Warren Vacation Rentals
-
Lenox Vacation Rentals
-
Stockbridge Vacation Rentals
-
West Stockbridge Vacation Rentals
-
Northampton Vacation Rentals
-
Amherst Vacation Rentals
-
Great Barrington Vacation Rentals
-
Hudson Vacation Rentals
-
Ashburnham Vacation Rentals
-
New Marlborough Vacation Rentals
-
Cabins in Catskill
-
Hubbardston Vacation Rentals
-
Sheffield Vacation Rentals
-
Lake Placid Vacation Rentals
-
Wilmington, NY Vacation Rentals
-
House Rentals in Burlington
-
Vacation Rentals in Windham
-
Springfield MA Vacation Rentals
-
Saranac Lake Vacation Rentals
-
Vacation Rentals in Stowe
-
Meredith Vacation Rentals
-
Laconia Vacation Rentals
-
Hunter Vacation Rentals
-
Weirs Beach Vacation Rentals
-
Manchester, NH Vacation Rentals
-
Saugerties Vacation Rentals
-
Lodging & Cabins in Tupper Lake
-
Morristown Vacation Rentals
-
House Rentals in Nashua
-
Gilford Vacation Rentals
-
Lodging & Cabins in Old Forge
-
Moultonborough Vacation Rentals
-
Accommodation in Cooperstown
Top Vacation Ideas
- Romantic Getaways in Ohio
- Bali Honeymoon
- Romantic Getaways in Pennsylvania
- Lake Havasu Spring Break Hotels & Vacation Rentals
- Romantic Getaways in Florida
- Romantic Getaways in Colorado
- Romantic Getaways in North Carolina
- Romantic Getaways in Virginia
- South Padre Island Spring Break Hotels & Vacation Rentals
- Romantic Getaways in Wisconsin
- Romantic Getaways in Georgia
Explore More Vacation Ideas
-
Lake Cabins in Texas
-
Weekend Getaway in the Northeast
-
New Orleans Monthly Rentals
-
Airbnbs in Goleta
-
Hotels in Wisconsin Dells
-
Airbnbs around Lewis Smith Lake
-
Bed and Breakfast Accommodation in Saint Augustine
-
Pet Friendly Rentals in Destin
-
Bed and Breakfast Accommodation in Connecticut
-
Airbnbs in Wild Dunes
-
Valentines in Denver
-
Valentines in Chicago
-
Bed and Breakfast Accommodation in Santa Barbara
-
Airbnbs in Sausalito
-
Family Vacation in Washington D.C.
-
Airbnbs in Eastham
-
Cabins with Hot Tubs in Broken Bow
-
Airbnbs in Gallatin
-
Airbnbs in Burlington
-
Bed and Breakfast Accommodation in Gainesville
-
Lake House Rentals in New Jersey