Rupert Vacation Rentals

Compare 15 available properties from 10 providers
Rupert
Anytime
2 guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Distance to center
Max. 1 mi
Max. 2 mi
Max. 3 mi
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Recommended Vacation Rentals in Rupert

Find your perfect vacation rental in Rupert: from $164 per night

House Rupert 19
House ∙ 19 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
from $631
e-domizil
View deal
House Rupert 12
House ∙ 12 guests ∙ 4 bedrooms
Rupert, Bennington County, Vermont, United States
from $350
Vrbo
5.0/5.0
"Excellent"
View deal
House Rupert 15
-30%
Dec 5 - Dec 12
House ∙ 15 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
from $333 $479
Vrbo
4.2/5.0
"Very good"
View deal
House Rupert 19
House ∙ 19 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
from $1,246
TUIvillas
View deal
See all offers

Vacation Houses With Pools

Apartment Pool Rupert
Pool
Apartment ∙ 6 guests ∙ 4 bedrooms
Rupert, Bennington County, Vermont, United States
from $185
Vrbo
4.7/5.0
"Outstanding"
View deal
House Pool Rupert
Pool
House ∙ 4 guests ∙ 2 bedrooms
Rupert, Bennington County, Vermont, United States
from $800
Vrbo
View deal
House Pool Rupert
Pool
House ∙ 10 guests ∙ 5 bedrooms
Rupert, Bennington County, Vermont, United States
from $243
Vrbo
4.9/5.0
"Excellent"
View deal
See all offers

Dog-Friendly Vacation Rentals

House Pet-friendly Rupert
-32%
May 8 - May 15
Pet-friendly
House ∙ 4 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
from $218 $323
Storied Stay
5.0/5.0
"Excellent"
View deal
House Pet-friendly Rupert
-33%
May 8 - May 15
Pet-friendly
House ∙ 8 guests ∙ 4 bedrooms
Rupert, Bennington County, Vermont, United States
from $430 $642
Storied Stay
5.0/5.0
"Excellent"
View deal
House Pet-friendly Rupert
Pet-friendly
House ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
from $233
Vrbo
5.0/5.0
"Excellent"
View deal
See all offers

Best vacation rentals with a balcony

House Balcony Rupert
-37%
Nov 6 - Nov 13
Balcony
House ∙ 4 guests ∙ 2 bedrooms
Rupert, Bennington County, Vermont, United States
from $294 $466
Storied Stay
5.0/5.0
"Excellent"
View deal
House Balcony Rupert
Balcony
House ∙ 12 guests ∙ 4 bedrooms
Rupert, Bennington County, Vermont, United States
from $162
Vrbo
5.0/5.0
"Excellent"
View deal
House Balcony Rupert
-28%
Dec 5 - Dec 12
Balcony
House ∙ 12 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
from $295 $406
Vrbo
5.0/5.0
"Excellent"
View deal
See all offers

Popular Rental Amenities in Rupert

  • Yard (6)
  • Internet (6)
  • Kitchen (5)
  • Grill (5)
  • Parking (5)
  • No smoking (5)
  • TV (4)
  • Fishing (4)
  • Washer (4)
  • Pet allowed (3)
  • Pool (3)
  • Fireplace (3)

Use filters to search and find an offer matching your requirements among all of the properties in Rupert. In Rupert, 16 properties include "internet". So, if you can't imagine a vacation without internet, use the internet filter to compare these rentals. Not as many accommodations in Rupert are available if you're dreaming of days spent poolside or if you plan to go fishing as "fishing" and "pools" are not often provided in Rupert.

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 December while the driest month is August.

Accommodations for your vacation in Rupert

6 among the 9 listed rentals in Rupert are house rentals. They account for most of the properties in this destination (85.71%). Interestingly, specific accommodation type, house rentals is $1,199 a night, with an average area of 4,300 ft². Furthermore, these accommodations are optimal for large groups, as most can accommodate 17 vacationers. If you are searching for another type of accommodation, you can find many other options, such as farmhouse rentals, which are the other very typical type of accommodation in Rupert. These accommodations cost $142 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.

Show all 15 properties
Where to find the best food in Rupert?

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.

What are the best places to discover the arts and culture of Rupert?

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.

Where are the unique attractions in Rupert?

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 2,000 providers, including:

Booking.com Vacation Rentals in Rupert TripAdvisor Vacation Rentals in Rupert Vrbo Vacation Rentals in Rupert Airbnb 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 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

Vacation Rentals

image-tag