Title: Rupert Vacation Rentals from $381: Search Short-Term Rentals | Expedia.com

[Rupert Travel Guide](https://expedia.com/Rupert.dx3000459728)[Hotels in Rupert](https://expedia.com/Rupert-Hotels.d3000459728.Travel-Guide-Hotels)[Flights to Rupert](https://expedia.com/Cheap-Flights-To-Rupert.d3000459728.Travel-Guide-Flights)[Car Rentals in Rupert](https://expedia.com/Car-Rentals-In-Rupert.d3000459728.Car-Rental-Guide)[Rupert Vacation Packages](https://expedia.com/Rupert.d3000459728.Destination-Travel-Guides)

![Vermont Foliage](https://images.trvl-media.com/place/3000459728/0596c53e-acf8-4425-a7ad-1840b2dc5352.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Rupert vacation rentals

![Outdoor spa tub](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/4994716e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snow and ski sports](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/1e2b3992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/a16eeef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms | Balcony](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/c46d6757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Long Trail House at Stratton Mountain Resort

[](https://www.expedia.com/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information)

Stratton

8.6/10

Excellent

(83 reviews)

"Nice place and great location!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William

$445 nightly

$503 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03&regionId=3000459728&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=CABIN)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=COTTAGE)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=VILLA)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America&regionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-05-17&d1=2026-05-17&endDate=2026-05-20&d2=2026-05-20&lodging=CHALET)

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## Top Rupert Hotel Reviews

![The Reluctant Panther Inn and Restaurant](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/8359157a_y.jpg)

### The Reluctant Panther Inn and Restaurant

10/10 Excellent

"Great stay, the lodge room was spacious and spotless with a huge bathroom and fireplace. Food in the restaurant was excellent. Would stay there again. "

[](https://expedia.com/Bennington-Hotels-The-Reluctant-Panther-Inn-And-Restaurant.h3908442.Hotel-Information)

![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg)

### Hampton Inn and Suites Manchester

10/10 Excellent

"Clean, staff friendly "

[](https://expedia.com/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information)

![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg)

### Aspen At Manchester

10/10 Excellent

"Solid updated motor lodge. Recommended"

[](https://expedia.com/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information)

![Sun Lodge](https://images.trvl-media.com/lodging/2000000/1160000/1157400/1157354/3e494820_y.jpg)

### Sun Lodge

10/10 Excellent

"Amazing boutique hotel, family friendly. Recreation room in basement, skiing bromley right there!"

[](https://expedia.com/Bennington-Hotels-The-Lodge-At-Bromley.h1157354.Hotel-Information)

![Brittany Motel](https://images.trvl-media.com/lodging/11000000/10540000/10533000/10532948/26d2b6f4_y.jpg)

### Brittany Motel

10/10 Excellent

"It was nice and comfortable "

[](https://expedia.com/Bennington-Hotels-Brittany-Motel.h10532948.Hotel-Information)

![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg)

### The Manchester View

10/10 Excellent

"Everything was perfect 👌 "

[](https://expedia.com/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information)

![Kimpton Taconic Hotel by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg)

### Kimpton Taconic Hotel by IHG

10/10 Excellent

"Best atmosphere and family stay ever. Kids friendly."

[](https://expedia.com/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information)

![The Inn at Manchester](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/534fcc92_y.jpg)

### The Inn at Manchester

10/10 Excellent

"What a lovely place! We loved the homey experience. The staff were kind and accommodating, breakfast was delicious, the bar was a nice place to unwind after a long day on the slopes and the room was spacious, clean and comfortable. Highly recommend, we will be back! "

[](https://expedia.com/Bennington-Hotels-The-Inn-At-Manchester.h1505817.Hotel-Information)

![The Olympia Lodge](https://images.trvl-media.com/lodging/10000000/9260000/9257700/9257616/c701f02d_y.jpg)

### The Olympia Lodge

10/10 Excellent

"Fantastic stay! Friendly staff, very cozy. "

[](https://expedia.com/Bennington-Hotels-The-Olympia-Lodge.h9257616.Hotel-Information)

## Find out more about Rupert

**Everything you need to know about Rupert vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rupert vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rupert vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Rupert vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Rupert. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Rupert in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $381 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Rupert rentals**

At Expedia, we put the best Rupert vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Rupert rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rupert vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rupert. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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- [Vacation Homes in Rupert ](https://expedia.com/Rupert-Private-Vacation-Homes.d3000459728-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Rupert ](https://expedia.com/Rupert-Cottages.d3000459728-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Rupert ](https://expedia.com/Rupert-Apartments.d3000459728-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Rupert ](https://expedia.com/Rupert-Condos.d3000459728-aaCondos.Travel-Guide-Accommodation)
- [Cabin Rentals in Rupert ](https://expedia.com/Rupert-Cabins.d3000459728-aaCabins.Travel-Guide-Accommodation)
- [Chalets in Rupert ](https://expedia.com/Rupert-Chalets.d3000459728-aaChalets.Travel-Guide-Accommodation)
- [B&B in Rupert ](https://expedia.com/Rupert-Bed-And-Breakfast.d3000459728-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Farmstay in Rupert ](https://expedia.com/Rupert-Agritourism.d3000459728-aaAgritourism.Travel-Guide-Accommodation)
- [Resorts in Rupert ](https://expedia.com/Rupert-Resorts.d3000459728-aaResorts.Travel-Guide-Accommodation)
- [Motels in Rupert ](https://expedia.com/Rupert-Motels.d3000459728-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Rupert ](https://expedia.com/Rupert-RV-Parks.d3000459728-aaRVParks.Travel-Guide-Accommodation)
- [Guest Houses in Rupert ](https://expedia.com/Rupert-Guest-Houses.d3000459728-aaGuestHouses.Travel-Guide-Accommodation)
- [Lodges in Rupert ](https://expedia.com/Rupert-Lodges.d3000459728-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Rupert ](https://expedia.com/Rupert-Apart-Hotels.d3000459728-aaApartHotels.Travel-Guide-Accommodation)
- [Villas in Rupert ](https://expedia.com/Rupert-Villas.d3000459728-aaVillas.Travel-Guide-Accommodation)
- [Inns in Rupert ](https://expedia.com/Rupert-Inns.d3000459728-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Rupert?

### What are some of the best vacation rentals in Rupert?

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### What’s there to see and do in Rupert?

### What’s a vacation rental in Rupert like?

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