Rupert Vacation Rentals

Compare 162 available properties from 21 providers
Rupert
Save up to 26%

Best Vacation Home Deals in Rupert

-26%
e.g. 12/1 - 12/8
House ∙ 19 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
from $729 $988
Only-apartments
4.9
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-25%
e.g. 5/25 - 6/1
House ∙ 19 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
from $632 $847
e-domizil
4.7
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Book the ideal vacation home for as little as $81 per night by searching among the 162 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 26%.

Recommended Vacation Rentals in Rupert

Rent a vacation accommodation in Rupert: from $81 per night

House ∙ 8 guests ∙ 4 bedrooms
Dorset, Bennington County, Vermont, United States
from $656
VRBO
4.2
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House ∙ 6 guests ∙ 3 bedrooms
Dorset, Bennington County, Vermont, United States
from $205
VRBO
5.0
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House ∙ 15 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
from $301
VRBO
4.3
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House ∙ 16 guests ∙ 6 bedrooms
Dorset, Bennington County, Vermont, United States
from $699
VRBO
5.0
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House ∙ 13 guests ∙ 2 bedrooms
Granville, Washington County, New York, United States
from $251
HomeAway
5.0
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Private room ∙ 6 guests ∙ 3 bedrooms
Granville, Washington County, New York, United States
from $126
HomeAway
5.0
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House ∙ 2 guests ∙ 2 bedrooms
Manchester Center, Manchester, Vermont, United States
from $394
VRBO
5.0
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Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Dorset, Bennington County, Vermont, United States
from $166
Booking.com
4.7
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Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Dorset, Bennington County, Vermont, United States
from $201
Booking.com
4.6
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 8 guests ∙ 4 bedrooms
Rupert, Bennington County, Vermont, United States
from $170
VRBO
5.0
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Fishing
House ∙ 8 guests ∙ 3 bedrooms
Dorset, Bennington County, Vermont, United States
from $253
VRBO
4.7
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Fishing
House ∙ 9 guests ∙ 4 bedrooms
Dorset, Bennington County, Vermont, United States
from $304
VRBO
5.0
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 3 guests ∙ 1 bedroom
Dorset, Bennington County, Vermont, United States
from $196
VRBO
5.0
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Fireplace
House ∙ 5 guests ∙ 2 bedrooms
West Pawlet, Pawlet, Vermont, United States
from $144
VRBO
4.9
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Fireplace
House ∙ 10 guests ∙ 4 bedrooms
West Pawlet, Pawlet, Vermont, United States
from $147
VRBO
4.9
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 12 guests ∙ 4 bedrooms
Rupert, Bennington County, Vermont, United States
from $422
VRBO
5.0
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Pet-friendly
House ∙ 8 guests ∙ 4 bedrooms
Dorset, Bennington County, Vermont, United States
from $368
VRBO
5.0
View deal
Pet-friendly
House ∙ 11 guests ∙ 4 bedrooms
Dorset, Bennington County, Vermont, United States
from $596
VRBO
5.0
View deal
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Popular Rental Amenities in Rupert

  • Internet (139)
  • Parking (139)
  • No smoking (138)
  • TV (136)
  • Kitchen (128)
  • Microwave (117)
  • Washer (109)
  • AC (108)
  • Dishwasher (103)
  • Fireplace (95)
  • Yard (90)
  • Grill (89)
Use filters to search and find an offer matching your requirements among all of the properties in Rupert. In Rupert, 160 properties include "internet". So, if you need internet access during your vacation, use the internet filter to compare these rentals. Not as many accommodations in Rupert are available if you want a rental with a pool or if you enjoy soaking in the hot tub as "Jacuzzis" and "pools" are not often provided in Rupert.

Price and Availability Index in Rupert

Vacation Rental Price Information in Rupert

The price graph will give you the nightly price average for the upcoming months of the year. The most expensive prices are in December (12/22 - 12/29). Prices reach an average of $436 per night. However, in August (8/17 - 8/24), prices decrease to an average of $364 per night.

Rental Availability Information in Rupert

Check how busy Rupert is with our availability graph. More people travel to Rupert a week in December (12/22 - 12/29). So far, 53% of the rentals are occupied this week. The week with the most available rentals is in February (2/23 - 3/2), with 87% of the vacation rentals available.

The Weather in Rupert

32°
12°
34°
12°
43°
21°
57°
34°
72°
48°
77°
54°
82°
59°
81°
57°
73°
48°
61°
39°
48°
28°
37°
23°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

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 July while the driest month is August.

Accommodations in Rupert

122 among the 162 listed rentals in Rupert are house rentals. They account for more than half of the properties in this destination (59.8%). Interestingly, specific accommodation type, house rentals is $566 a night, with an average area of 3,000 ft². Furthermore, these accommodations are optimal for large groups, as most can accommodate 10 vacationers. If you are searching for another type of accommodation, you can find many other options, such as hotel rooms, which are the other very typical type of accommodation in Rupert. These accommodations cost $233 per night on average and have an average size of 320 ft².

Rupert vacation homes in the setting of Vermont's natural beauty

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.

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Food & Drinks

Apple pies and cider

If you are in Vermont, you cannot leave until you have tasted the apples and the dishes made from locally grown apples. Your vacation at Rupert will familiarize you with apple cider, apple pie, as well as baked items made from apples. The Dutton Berry Farmstands in Manchester is a good place to visit if you love orchards and apples. Throughout the area, you will come across farms selling dishes made from local produce such as corn, strawberries and squash.

Art & Culture

Explore the museums in and around Rupert

The Bennington Museum displays works of craft such as glassware, pottery, and woodcrafts. The museum is located inside a decommissioned train station, and close to the downtown city area.

Another attraction is the Bennington Center for the Arts, with exhibitions of paintings by local and American artists, as well as a historical museum of covered bridges, a typical architectural feature of the area.

One of the notable attractions of the city lies in nearby Manchester where you can visit the home of the Abraham Lincoln's family.

Local Attractions

Golf courses in Rupert

Rupert and surrounding areas have plenty of golf courses. You can play a round at the public golf courses or choose memberships at the private facilities.

The Mount Snow Country Club has been helping golfers perfect their skills and enjoy the game since the 1970s. You might also like to try your hand at the sport in the Ekwanok Country Club.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Rupert VRBO Vacation Rentals in Rupert HomeAway Vacation Rentals in Rupert TripAdvisor Vacation Rentals in Rupert VacationRentals.com Vacation Rentals in Rupert HouseTrip Vacation Rentals in Rupert FlipKey Vacation Rentals in Rupert 9flats.com Vacation Rentals in Rupert VaycayHero Vacation Rentals in Rupert PerfectPlaces.com Vacation Rentals in Rupert Homestay.com Vacation Rentals in Rupert Only-apartments Vacation Rentals in Rupert Interhome Vacation Rentals in Rupert Bedycasa Vacation Rentals in Rupert Novasol Vacation Rentals in Rupert HomeEscape Vacation Rentals in Rupert

Vacation Destinations Near Rupert