Title: Rupert Vacation Rentals from $306: 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)

![](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

[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 two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-07-24&endDate=2026-07-26&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

![TV, books](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/defca110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/614084d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/79c166d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/6958837e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Cottage Retreat

[](https://www.expedia.com/Cambridge-Hotels-Peaceful-Cottage-Retreat.h33734584.Hotel-Information)

cambridge

9.8/10

Exceptional

(47 reviews)

"Perfect little stay. Best parts of being out in the middle of the woods that also has great cell service. Everything you'd need to enjoy a couple days out in "

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

Victor L.

$170 nightly

$189 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Cambridge-Hotels-Peaceful-Cottage-Retreat.h33734584.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107180000/107179800/107179793/b93f8a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107180000/107179800/107179793/16edb5ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/108000000/107180000/107179800/107179793/95908bc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107180000/107179800/107179793/b208aaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy cabin in charming Londonderry

[](https://www.expedia.com/Londonderry-Hotels-Cozy-Cabin-In-Charming-Londonderry.h107179793.Hotel-Information)

Londonderry

8.4/10

Very Good

(5 reviews)

"Very cozy and quiet. "

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

Eric H.

$243 nightly

$274 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Cozy-Cabin-In-Charming-Londonderry.h107179793.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/620d544b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/a4954c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/5f732777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/cea2d009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

[](https://www.expedia.com/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.Hotel-Information)

Stratton

7.8/10

Good

(57 reviews)

"Location was great, pool, hot tubs and sauna were great"

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

Lin M.

$215 nightly

$243 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.Hotel-Information)

![Children's area](https://images.trvl-media.com/lodging/108000000/107450000/107448700/107448633/1b417e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/108000000/107450000/107448700/107448633/2da73c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107450000/107448700/107448633/965a693c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107450000/107448700/107448633/c7526449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Bromley Retreat

[](https://www.expedia.com/Peru-Hotels-Charming-One-Bedroom-Condo-On-Bromley-Mountain.h107448633.Hotel-Information)

Bromley Mountain

9.6/10

Exceptional

(12 reviews)

"Great location, steps to the Plaza trail, clean and well stocked with kitchen gear, towels etc. The furniture is a little dated but overall a great place to stay! Loved it!"

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

Barb C.

$288 nightly

$325 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Peru-Hotels-Charming-One-Bedroom-Condo-On-Bromley-Mountain.h107448633.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74110000/74100100/74100040/98181c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74110000/74100100/74100040/98d2d233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74110000/74100100/74100040/74c7fd79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74110000/74100100/74100040/cda234b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

[](https://www.expedia.com/Stratton-Hotels-Mountain-View-Condo-With-Fast-WiFi.h74100040.Hotel-Information)

Stratton

7.4/10

Good

(21 reviews)

"A great weekend. The property was clean and comfortable."

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

Joan P.

$343 nightly

$387 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-Mountain-View-Condo-With-Fast-WiFi.h74100040.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/90000000/89070000/89068200/89068117/245ee0c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89070000/89068200/89068117/a7539bc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89070000/89068200/89068117/2ffb8ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/90000000/89070000/89068200/89068117/2f6c29d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

[](https://www.expedia.com/Londonderry-Hotels-Summit-View-Cottage-Close-To-Stratton-Mountain.h89068117.Hotel-Information)

Londonderry

10/10

Exceptional

(10 reviews)

"Great location, well-designed house, and a beautiful view."

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

Marcel P.

$568 nightly

$641 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Summit-View-Cottage-Close-To-Stratton-Mountain.h89068117.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103590000/103582500/103582490/1b33e3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103590000/103582500/103582490/w1179h1473x0y0-1190758b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/104000000/103590000/103582500/103582490/2382fc0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103590000/103582500/103582490/e1e135fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Romantic Riverbed Treehouse - hot tub & new sauna!

[](https://www.expedia.com/Londonderry-Hotels-Romantic-Riverbed-Treehouse-Hot-Tub-New-Sauna.h103582490.Hotel-Information)

londonderry

9.0/10

Wonderful

(6 reviews)

"Great little space"

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

John

$575 nightly

$650 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Romantic-Riverbed-Treehouse-Hot-Tub-New-Sauna.h103582490.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/f8d749ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/916d5cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/bf43c699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/90000000/89550000/89541000/89540910/dc8751a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely ski-in/out condo steps from ski lift with trails and amazing views

[](https://www.expedia.com/Stratton-Hotels-Lovely-Ski-Inout-Condo-Steps-From-Ski-Lift-With-Trails-And-Amazing-Views.h89540910.Hotel-Information)

Stratton

8.4/10

Very Good

(32 reviews)

"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."

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

John N.

$271 nightly

$306 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-Lovely-Ski-Inout-Condo-Steps-From-Ski-Lift-With-Trails-And-Amazing-Views.h89540910.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103490000/103490000/103489995/3081d55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103490000/103490000/103489995/ff9732b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103490000/103490000/103489995/6bdd91f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103490000/103490000/103489995/179138f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Insanely romantic treehouse perched next to a stream and rolling hills.

[](https://www.expedia.com/Londonderry-Hotels-Insanely-Romantic-Treehouse-Perched-Next-To-A-Stream-And-Rolling-Hills.h103489995.Hotel-Information)

Londonderry

10/10

Exceptional

(2 reviews)

"Very nice secluded treehouse. We would definitely recommend!"

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

Beth H.

$790 nightly

$893 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Insanely-Romantic-Treehouse-Perched-Next-To-A-Stream-And-Rolling-Hills.h103489995.Hotel-Information)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/3e9df2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/0444e51c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/29b5b165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/098ed9b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

[](https://www.expedia.com/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.Hotel-Information)

Londonderry

7.0/10

Good

(2 reviews)

"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "

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

Christine M.

$444 nightly

$501 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w906h683x59y0-81ea00c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w904h683x60y0-62d4a56d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w905h683x60y0-69b1532d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89710000/89700500/89700465/w505h683x260y0-3895f5aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Stay at Birds of a Feather Farm & Spa 

[](https://www.expedia.com/Shaftsbury-Hotels-Peaceful-Country-Getaway-Birds-Of-A-Feather-Farm.h89700465.Hotel-Information)

Shaftsbury

9.8/10

Exceptional

(32 reviews)

"Great place!!"

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

Margaret D.

$213 nightly

$238 total

May 3 - May 4

Total with taxes and fees

[](https://www.expedia.com/Shaftsbury-Hotels-Peaceful-Country-Getaway-Birds-Of-A-Feather-Farm.h89700465.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/f5d0c9b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/ef649af5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/6beaf5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/464b1801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

[](https://www.expedia.com/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information)

Jamaica

9.6/10

Exceptional

(25 reviews)

"I stayed here for a few days in October with friends. We had some initial confusion with the door locks, but the hosts were able to resolve it quickly.Great location, tons of sleeping and living space, and the hot tub was a welcome addition. We had a great time and would recommend this spot."

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

Jonathan E.

$793 nightly

$896 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/39000000/38840000/38839300/38839270/423b678f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/39000000/38840000/38839300/38839270/4bfc8590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/39000000/38840000/38839300/38839270/1e5eab43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/39000000/38840000/38839300/38839270/c28fac4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious apartment in beautiful, historic Arlington VT

[](https://www.expedia.com/Bennington-Hotels-Spacious-Apartment-In-Beautiful.h38839270.Hotel-Information)

Arlington

10/10

Exceptional

(61 reviews)

"This home was spacious, super clean, and in a great location. "

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

Des C.

$218 nightly

$244 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Bennington-Hotels-Spacious-Apartment-In-Beautiful.h38839270.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88310000/88304400/88304398/922d40ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88310000/88304400/88304398/2ec0429d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88310000/88304400/88304398/2018eac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/89000000/88310000/88304400/88304398/4830e6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton Mtn Studio | Renovated | Walk to Lifts

[](https://www.expedia.com/Stratton-Hotels-Stratton-Studio-Newly-Renovated-Walk-To-Lifts.h88304398.Hotel-Information)

Stratton Mountain

10/10

Exceptional

(31 reviews)

"Great location."

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

Jeffrey

$382 nightly

$431 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-Stratton-Studio-Newly-Renovated-Walk-To-Lifts.h88304398.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/31000000/30450000/30441500/30441410/fbc19381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/31000000/30450000/30441500/30441410/ba659a51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/31000000/30450000/30441500/30441410/209d0106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/31000000/30450000/30441500/30441410/3c770e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Vermont A-Frame Mountain Retreat

[](https://www.expedia.com/Bondville-Hotels-The-Vermont-A-Frame-Mountain-Retreat.h30441410.Hotel-Information)

Winhall

9.8/10

Exceptional

(27 reviews)

"Great home, perfect weekend away at Stratton. Host was great and so was the property"

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

Kevin M.

$516 nightly

$544 total

Apr 16 - Apr 17

Total with taxes and fees

[](https://www.expedia.com/Bondville-Hotels-The-Vermont-A-Frame-Mountain-Retreat.h30441410.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/127000000/126780000/126773100/126773059/eec23673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126780000/126773100/126773059/db0bd570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/127000000/126780000/126773100/126773059/48833132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/127000000/126780000/126773100/126773059/debb55be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

[](https://www.expedia.com/Wallingford-Hotels-Quiet-Apt-Close-To-Okemo-And-Killington-Off-Rt-7-With-Private-Driveway.h126773059.Hotel-Information)

Wallingford

$156 nightly

$174 total

Apr 3 - Apr 4

Total with taxes and fees

[](https://www.expedia.com/Wallingford-Hotels-Quiet-Apt-Close-To-Okemo-And-Killington-Off-Rt-7-With-Private-Driveway.h126773059.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/127000000/126630000/126624000/126623945/a7755447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/127000000/126630000/126624000/126623945/9c1c0ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/127000000/126630000/126624000/126623945/2005e8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/127000000/126630000/126624000/126623945/0823414a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

[](https://www.expedia.com/Stratton-Hotels-Walk-To-Lifts.h126623945.Hotel-Information)

Stratton

8.0/10

Very Good

(1 review)

"Great location and covered parking. "

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

Jonathan M.

$175 nightly

$197 total

Apr 7 - Apr 8

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-Walk-To-Lifts.h126623945.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/119000000/118930000/118925300/118925261/cacc5348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/119000000/118930000/118925300/118925261/a8509aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118930000/118925300/118925261/aedd8286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118925300/118925261/58607bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Mountain Retreat w/ Chef’s Kitchen

[](https://www.expedia.com/Manchester-Center-Hotels-Modern-Mountain-Retreat-W-Chefs-Kitchen.h118925261.Hotel-Information)

Manchester

$353 nightly

$399 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Manchester-Center-Hotels-Modern-Mountain-Retreat-W-Chefs-Kitchen.h118925261.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/119000000/118760000/118754500/118754448/527e393f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/119000000/118760000/118754500/118754448/1a688f8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/119000000/118760000/118754500/118754448/8ea0f7e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118760000/118754500/118754448/f0755ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Home with Colonial Charm in Manchester

[](https://www.expedia.com/Manchester-Center-Hotels-Historic-Home-With-Colonial-Charm-In-Manchester.h118754448.Hotel-Information)

Manchester

$336 nightly

$380 total

Apr 15 - Apr 16

Total with taxes and fees

[](https://www.expedia.com/Manchester-Center-Hotels-Historic-Home-With-Colonial-Charm-In-Manchester.h118754448.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/6bb1cc24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/399ba60a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/fdf153b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/deccb16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

[](https://www.expedia.com/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information)

Stratton

10/10

Exceptional

(6 reviews)

"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "

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

Nicholas D.

$659 nightly

$745 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.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=2026-04-16&endDate=2026-04-17&regionId=3000459728&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## 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=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=CABIN)

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=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&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=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&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=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=COTTAGE)

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=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=APARTMENT)

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=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=APART_HOTEL)

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=2026-07-01&d1=2026-07-01&endDate=2026-07-04&d2=2026-07-04&lodging=CHALET)

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## Top Rupert Hotel Reviews

![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/4412313e_y.jpg)

### The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"it's all good"

[](https://expedia.com/Bennington-Hotels-The-Palmer-House-Resort.h6028480.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

8/10 Good

"Great business center and laundry facilities. "

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

![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg)

### The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Amazing hotel"

[](https://expedia.com/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information)

![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/cbf700aa_y.jpg)

### Aspen At Manchester

10/10 Excellent

"Excellent location, v"

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

![Four Winds Country Motel](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640832/c7e6e735_y.jpg)

### Four Winds Country Motel

6/10 Okay

"Basic place to stay. Fine for one night. Bathroom was clean. Bed was comfortable. "

[](https://expedia.com/Bennington-Hotels-Four-Winds-Country-Motel.h7640832.Hotel-Information)

![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56_y.jpg)

### The Manchester View

10/10 Excellent

"The "

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

![The Reluctant Panther Inn and Restaurant](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/b36aec9e_y.jpg)

### The Reluctant Panther Inn and Restaurant

10/10 Excellent

"It feels like home when we stay here. The staff is friendly and welcoming. Our room was upgraded and we loved the fireplace and jacuzzi tub! Breakfast is delivered right to your room in a lovely picnic basket. This was our second stay. We will definitely be back. "

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

![Weathervane Motel](https://images.trvl-media.com/lodging/11000000/10430000/10429400/10429394/17ddc189_y.jpg)

### Weathervane Motel

6/10 Okay

"Took 5 minutes for w"

[](https://expedia.com/Bennington-Hotels-Weathervane-Motel.h10429394.Hotel-Information)

![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/fddf0cb9_y.jpg)

### The Equinox Golf Resort & Spa

10/10 Excellent

"We love the Equinox. We usually stay here during ski season. Always looking forward to rest after a long day of ski. Amenities are amazing, the restaurant and bar are great to eat and hangout. "

[](https://expedia.com/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.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 $306 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.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [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)
- [Condo Rentals in Rupert ](https://expedia.com/Rupert-Condos.d3000459728-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Rupert ](https://expedia.com/Rupert-Apartments.d3000459728-aaApartments.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)
- [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)
- [Farmstay in Rupert ](https://expedia.com/Rupert-Agritourism.d3000459728-aaAgritourism.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)
- [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)
- [Aparthotels in Rupert ](https://expedia.com/Rupert-Apart-Hotels.d3000459728-aaApartHotels.Travel-Guide-Accommodation)

## Frequently asked questions

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

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

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- [Best Hotels in Colchester](https://expedia.com/Colchester-Hotels.d91135.Travel-Guide-Hotels)
- [Best Hotels in Woodstock](https://expedia.com/Woodstock-Hotels.d10868.Travel-Guide-Hotels)
- [Best Hotels in Springfield](https://expedia.com/Springfield-Hotels.d10292.Travel-Guide-Hotels)
- [Best Hotels in Manchester](https://expedia.com/Manchester-Hotels.d129374.Travel-Guide-Hotels)
- [Best Hotels in Williston](https://expedia.com/Williston-Hotels.d10411.Travel-Guide-Hotels)
- [Best Hotels in Killington](https://expedia.com/Killington-Hotels.d10780.Travel-Guide-Hotels)
- [Best Hotels in Burlington](https://expedia.com/Burlington-Hotels.d601763.Travel-Guide-Hotels)
- [Best Hotels in Middlebury](https://expedia.com/Middlebury-Hotels.d8852.Travel-Guide-Hotels)
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Flights

- [Flights to BTV](https://expedia.com/Cheap-Flights-To-Stowe.d6057386.Travel-Guide-Flights)
- [Flights to BTV](https://expedia.com/Cheap-Flights-To-Burlington.d601763.Travel-Guide-Flights)

Cars

- [Car rentals in Burlington](https://expedia.com/Car-Rentals-In-Burlington.d601763.Car-Rental-Guide)

Activities

- [Things to do in Montpelier](https://expedia.com/Things-To-Do-In-Montpelier.d8798.Travel-Guide-Activities)

Vacation Rentals

- [Vacation Rentals Killington](https://expedia.com/Killington-Vacation-Rentals.d10780.Travel-Guide-VacationRentals)

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