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Rupert Vacation Rentals

Find 15 available offers from 13 partners
Rupert
Anytime
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+
Save up to 67%

Best Vacation Home Deals in Rupert

House Rupert
Apr 2 - Apr 9
-51%
$882
$433 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
"Excellent" (127 ratings)
Rupert, Bennington County, Vermont, United States
Free cancellation
Details
Storied Stay
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Resort Rupert
May 27 - Jun 3
-58%
$609
$256 per night
Resort ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
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HomeToGo
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Resort Rupert
Apr 2 - Apr 9
-67%
$680
$223 per night
Resort ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Details
HomeToGo
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Book the ideal vacation home for as little as $152 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 56%.

Recommended Vacation Rentals in Rupert

Find your perfect vacation rental in Rupert: from $152 per night

Villa Rupert
$1,086 per night
Villa ∙ 15 guests ∙ 6 bedrooms
Rupert, Bennington County, Vermont, United States
Details
HomeToGo
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House Rupert
$356 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
"Excellent" (60 ratings)
Rupert, Bennington County, Vermont, United States
Details
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House Rupert
$345 per night
House ∙ 8 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Details
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House Rupert
$198 per night
House ∙ 8 guests ∙ 3 bedrooms
4.1
"Very good" (39 ratings)
Rupert, Bennington County, Vermont, United States
Details
Vacasa
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House Rupert
$688 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (10 ratings)
Rupert, Bennington County, Vermont, United States
Details
Vacasa
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Resort Rupert
$236 per night
Resort ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Details
HomeToGo
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Resort Rupert
$208 per night
Resort ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Details
HomeToGo
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Resort Rupert
$246 per night
Resort ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Details
HomeToGo
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Resort Rupert
$266 per night
Resort ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Details
HomeToGo
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Vacation Houses With Pools

Motel Pool Rupert
Jun 18 - Jun 25
-30%
$188
$131 per night
Motel ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Pool
Details
HomeToGo
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Motel Pool Rupert
Apr 2 - Apr 9
-46%
$188
$102 per night
Motel ∙ 3 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Pool
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HomeToGo
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Motel Pool Rupert
Apr 2 - Apr 9
-43%
$212
$121 per night
Motel ∙ 4 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Pool
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Dog-Friendly Vacation Rentals

House Pet-friendly Rupert
Sep 2 - Sep 9
$445 per night
House ∙ 8 guests ∙ 4 bedrooms
Rupert, Bennington County, Vermont, United States
Free cancellation
Pet-friendly
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TripAdvisor
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Best vacation rentals with a balcony

Motel Balcony Rupert
$132 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.7
"Good" (175 ratings)
Rupert, Bennington County, Vermont, United States
Balcony
Details
Expedia
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Motel Balcony Rupert
$174 per night
Motel ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Balcony
Details
HomeToGo
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Bed & Breakfast Balcony Rupert
$356 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Rupert, Bennington County, Vermont, United States
Balcony
Details
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Popular Rental Amenities in Rupert

  • Internet (7)
  • Kitchen (7)
  • TV (7)
  • Washer (7)
  • Grill (6)
  • Fireplace (6)
  • Microwave (6)
  • Yard (5)
  • Balcony/Patio (5)
  • Dishwasher (5)
  • Pool (4)
  • Fishing (3)

Use filters to search and find an offer matching your requirements among all of the properties in Rupert. In Rupert, 7 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 to go fishing or if you travel with your pet as "pets Allowed" and "fishing" 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, 17 Jan
33°
21°

15%

0 h

18 mi/h

Tue, 18 Jan
10°
-4°

10%

9 h

6 mi/h

Wed, 19 Jan
32°

15%

0 h

6 mi/h

Thu, 20 Jan
14°

15%

3 h

6 mi/h

Fri, 21 Jan
-11°

15%

5 h

4 mi/h

Sat, 22 Jan
-13°

5%

9 h

3 mi/h

Sun, 23 Jan
24°

15%

1 h

3 mi/h

Accommodations for your vacation in Rupert

4 among the 15 listed rentals in Rupert are house rentals. They account for many of the properties in this destination (66.67%). Interestingly, specific accommodation type, house rentals is $1,173 a night, with an average area of 4,330 ft². Furthermore, these accommodations are optimal for large groups, as most can accommodate 14 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.

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 $152.

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 internet, TVs, and grills when booking a vacation rental in Rupert.

Are pets allowed in vacation rentals in Rupert?

Finding a cabin rental in Rupert that allows dogs is definitely possible, with 2 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 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

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