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Rupert Vacation Rentals

Find 15 available offers from 11 partners
Rupert
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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+

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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Save up to 57%

Best Vacation Home Deals in Rupert

House Rupert
Aug 14 - Aug 21
-22%
$322
$250 per night
House ∙ 8 guests ∙ 2 bedrooms
Rupert, Bennington County, Vermont, United States
Details
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House Rupert
Mar 25 - Apr 1
-57%
$463
$201 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
"Excellent" (16 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
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House Rupert
Oct 1 - Oct 8
-24%
$550
$418 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (35 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
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Book the ideal vacation home for as little as $132 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 61%.

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Top-Rated Rentals and Accommodations in Rupert

Cottage Rupert
Jun 17 - Jun 24
-55%
$281
$126 per night
Cottage ∙ 8 guests ∙ 2 bedrooms
4.8
"Excellent" (4 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
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House Rupert
Jul 30 - Aug 6
$246 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Rupert, Bennington County, Vermont, United States
Free cancellation
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House Rupert
Mar 25 - Apr 1
-30%
$241
$169 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Rupert, Bennington County, Vermont, United States
Free cancellation
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Recommended Vacation Rentals in Rupert

Find your perfect vacation rental in Rupert: from $132 per night

Villa Rupert
$593 per night
Villa ∙ 15 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
Details
Evolve
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House Rupert
$463 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
"Excellent" (25 ratings)
Rupert, Bennington County, Vermont, United States
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Condo Rupert
$233 per night
Condo ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (4 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
$154 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (3 ratings)
Rupert, Bennington County, Vermont, United States
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Farmhouse Rupert
$254 per night
Farmhouse ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (24 ratings)
Rupert, Bennington County, Vermont, United States
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Apartment Rupert
$153 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.8
"Excellent" (18 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
$181 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
"Excellent" (46 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
$355 per night
House ∙ 13 guests ∙ 1 bedroom
4.9
"Excellent" (51 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
$227 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
"Excellent" (8 ratings)
Rupert, Bennington County, Vermont, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Rupert

Apartment Rupert
$148 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
"Excellent" (14 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
$406 per night
House ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (26 ratings)
Rupert, Bennington County, Vermont, United States
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House Rupert
$388 per night
House ∙ 7 guests ∙ 4 bedrooms
4.7
"Outstanding" (52 ratings)
Rupert, Bennington County, Vermont, United States
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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.

House Balcony Rupert
Nov 5 - Nov 12
$475 per night
House ∙ 9 guests ∙ 4 bedrooms
4.9
"Excellent" (29 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Balcony
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House Balcony Rupert
Mar 18 - Mar 25
$232 per night
House ∙ 12 guests ∙ 4 bedrooms
4.8
"Excellent" (24 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Balcony
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House Balcony Rupert
Mar 18 - Mar 25
$243 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
"Excellent" (21 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Balcony
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Vacation homes and cottages with a garden

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Rupert with private yards.

House Yard Rupert
Mar 25 - Apr 1
$350 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (41 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Yard
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House Yard Rupert
Dec 17 - Dec 24
$246 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Rupert, Bennington County, Vermont, United States
Free cancellation
Yard
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House Yard Rupert
Mar 25 - Apr 1
$405 per night
House ∙ 9 guests ∙ 4 bedrooms
5.0
"Excellent" (86 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Yard
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Vacation Homes With Fishing Spots Nearby

Hoping to catch a few fish on your next vacation? Check out these amazing rentals in Rupert with fishing spots nearby.

Apartment Fishing Rupert
Dec 17 - Dec 24
$243 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.9
"Excellent" (47 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Fishing
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House Fishing Rupert
Dec 17 - Dec 24
$356 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (39 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Fishing
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House Fishing Rupert
Mar 18 - Mar 25
$485 per night
House ∙ 17 guests ∙ 7 bedrooms
4.6
"Outstanding" (43 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Fishing
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Popular Rental Amenities in Rupert

  • Kitchen (6)
  • Pet allowed (4)
  • Fireplace (4)
  • Internet (4)
  • TV (4)
  • Washer (4)
  • Microwave (4)
  • Pool (3)
  • Grill (3)
  • Yard (3)
  • Air conditioning (2)
  • No pets (2)

Use filters to search and find an offer matching your requirements among all of the properties in Rupert. In Rupert, 4 properties include "Pets allowed". So, if you travel with your pet, use the Pets allowed filter to compare these rentals. Not as many accommodations in Rupert are available if you love to grill out or if you want a rental with a yard as "Yard" and "Grill" are not often provided in Rupert.

The Weather in Rupert

max.
Min.
32°
12°
15 days 15
max.
Min.
34°
12°
13 days 13
max.
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43°
21°
13 days 13
max.
Min.
57°
34°
12 days 12
max.
Min.
72°
48°
14 days 14
max.
Min.
77°
54°
15 days 15
max.
Min.
82°
59°
14 days 14
max.
Min.
81°
57°
11 days 11
max.
Min.
73°
48°
11 days 11
max.
Min.
61°
39°
14 days 14
max.
Min.
48°
28°
11 days 11
max.
Min.
37°
23°
19 days 19
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.

7-Day Weather Forecast in Rupert

Mon, 27 Jun
73°
60°

15%

5 h

10 mi/h

Tue, 28 Jun
69°
55°

15%

8 h

4 mi/h

Wed, 29 Jun
77°
59°

15%

8 h

7 mi/h

Thu, 30 Jun
73°
59°

15%

10 h

3 mi/h

Fri, 1 Jul
82°
64°

0%

8 h

9 mi/h

Sat, 2 Jul
69°
64°

15%

0 h

4 mi/h

Sun, 3 Jul
73°
59°

0%

12 h

6 mi/h

Accommodations for your vacation in Rupert

1 among the 15 listed rentals in Rupert are house rentals. They account for more than half of the properties in this destination (50%). Interestingly, specific accommodation type, house rentals is $989 a night, with an average area of 4,000 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 apartment rentals, which are the other very typical type of accommodation in Rupert. These accommodations cost $1,161 per night on average and have an average size of 4,500 ft².
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.

Frequently Asked Questions

How much does it cost to rent a vacation rental in Rupert?

The average nightly price for vacation rentals in Rupert is $132.

How many vacation rentals are available to book in Rupert?

There are currently 15 vacation homes in Rupert to browse and book for your next trip.

What amenities are most popular for vacation homes in Rupert?

Most travelers search for Pets allowed, Fireplace, and Internet when booking a vacation rental in Rupert.

How many vacation rentals are in Rupert?

Rupert has 15 House rentals and Apartment rentals on offer to rent.

Are pets allowed in vacation rentals in Rupert?

Finding a cabin rental in Rupert that allows dogs is definitely possible, with 4 pet-friendly homes on offfer.

What's the best time of year to travel to Rupert?

July and August are typically the warmest months in Rupert with temperatures around 82 °F. January and February in Rupert are the coldest, with 12 °F on average.

We list offers from thousands of providers, including:

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

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