Search Vacation Homes in Rupert

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 424 Vacation Homes in Rupert with updated reviews, rates, and availability.

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AED 744
AED 2,365 total
includes taxes & fees
3 Jun - 4 Jun
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
TV, fireplace

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

8.6 out of 10, Excellent, (4)
"House was great. We were able to walk up the road with our skis and drop right in. I’d definitely stay here again."
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
Room for the whole family 8 minutes to Manchester
Terrace/patio

Room for the whole family 8 minutes to Manchester

10.0 out of 10, Exceptional, (3)
"Very priceable and great house with 5 bedrooms - each rooms are big and clean! Love it! Will come back again for next ski plan"
Room for the whole family 8 minutes to Manchester
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Exterior

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

10.0 out of 10, Exceptional, (167)
"We really enjoyed our stay - everything was great, clean, and it's really a wonderful property."
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Fridge, microwave, oven, stovetop

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

10.0 out of 10, Exceptional, (117)
"We have stayed here at least three times, and enjoy it every time. "
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!
Miscellaneous

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

10.0 out of 10, Exceptional, (1)
"We had such a lovely time in this well loved cabin. Super quiet location and well stocked with everything we needed for our end of year ski trip in Stratton. The owner was very friendly and helpful. We hope we will be back soon!"
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!
7200 sf Villa & Barn on 4 Acre Manchester Estate
Interior

7200 sf Villa & Barn on 4 Acre Manchester Estate

9.6 out of 10, Exceptional, (8)
"This rental was stunning! Such a cool property with so many different spaces for a large group to spend time. Everything was labeled for ease of access (very grateful for this!), we enjoyed many of the amenities, and communication with the host was fast! Wonderful stay with no issues!H"
7200 sf Villa & Barn on 4 Acre Manchester Estate
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
TV, fireplace, video games

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

10.0 out of 10, Exceptional, (18)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
Property grounds

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

8.8 out of 10, Excellent, (18)
"Property out and peaceful and quiet. View is great thanks."
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Fridge, microwave, oven, stovetop

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

9.6 out of 10, Exceptional, (7)
"The property is secluded but close enough to shops and restaurants. The deck is amazing with a jacuzzi and lounge chairs overlooking the golf course and mountains! Would definitely stay at again!"
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub
Exterior

Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub

10.0 out of 10, Exceptional, (25)
"We rented this property as a way to spend time with family right before the busy holiday season. We couldn’t have picked a better place to stay. The house was very cozy, clean, and had everything we needed and more! Check-in was super easy, and the host responded very quickly. The hot tub and sauna were great additions, but the view of the lake and mountains every morning was just what we wanted. We will definitely be recommending to friends and family!! "
Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Interior

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (22)
"Place was great and accommodating, would recommend. Thank you!"
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Luxury 4-BR Mountain Estate 10-min to Manchester
Miscellaneous

Luxury 4-BR Mountain Estate 10-min to Manchester

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a last minute booking as our original booking was canceled. It has been a very positive experience with communication, timely responses to questions, the property is immaculately clean, inviting with comfortable rooms. Kitchen well stocked and the outside property was beautiful. Unfortunately it rained so could not fully experience it. Definitely recommend "
The price is AED 1,286
AED 3,480 total
includes taxes & fees
29 Jun - 30 Jun
Luxury 4-BR Mountain Estate 10-min to Manchester
Big Green Barn - Artist's Barn in Manchester Village Vermont.
Interior

Big Green Barn - Artist's Barn in Manchester Village Vermont.

Big Green Barn - Artist's Barn in Manchester Village Vermont.
Serene Escape: Hot Tub | Barrel Sauna | Golf
Property grounds

Serene Escape: Hot Tub | Barrel Sauna | Golf

10.0 out of 10, Exceptional, (15)
"Great house! Nice bedrooms and accommodations including open living space, kids game room in basement, hot tub and sauna. Very conveniently located from Stratton mountain on shuttle line. Only comment would be for hosts to think through some more simple daily items such as hooks for coats, dressers in bedrooms for clothing, etc "
Serene Escape: Hot Tub | Barrel Sauna | Golf
Gather Together – Stratton Mtn Luxury & Comfort with a View
Exterior

Gather Together – Stratton Mtn Luxury & Comfort with a View

8.0 out of 10, Very Good, (5)
"Lots of Room, Clean, 5 min to the Slopes, we will stay here again!"
Gather Together – Stratton Mtn Luxury & Comfort with a View
Londonderry Vacation Home w/ Deck + Gas Grill!
Fridge, microwave, stovetop, dishwasher

Londonderry Vacation Home w/ Deck + Gas Grill!

6.0 out of 10, (1)
Londonderry Vacation Home w/ Deck + Gas Grill!
Cozy ski home with amazing views of Stratton & Bromley Mountains.
Property grounds

Cozy ski home with amazing views of Stratton & Bromley Mountains.

9.4 out of 10, Exceptional, (30)
"The convenient near-mountain location and living room views are hard to beat; the hot tub was a great touch as well! It was perfect for our large group over a holiday weekend."
Cozy ski home with amazing views of Stratton & Bromley Mountains.
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9 bedrooms, desk, iron/ironing board, free WiFi

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (22)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Property grounds

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

9.6 out of 10, Exceptional, (14)
"Happy experience and plenty of room. Everyone enjoyed the lake and sounding places."
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free