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Browse Select Rutland Holiday Homes

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

The price is £311
includes taxes & fees
18 Aug - 19 Aug
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

5-15 Minutes from Mountains, Balcony, Fireplace, Fast Wifi

The price is £235
includes taxes & fees
20 Aug - 21 Aug
5-15 Minutes from Mountains, Balcony, Fireplace, Fast Wifi

Acres & Views! Firepit, BBQ | Bayley Way Getaway

The price is £520
includes taxes & fees
18 Aug - 19 Aug
Acres & Views! Firepit, BBQ | Bayley Way Getaway

Three Decks Hot Tub Fire Table | DeckHouse Retreat

The price is £780
includes taxes & fees
18 Aug - 19 Aug
Three Decks Hot Tub Fire Table | DeckHouse Retreat

Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

9.8 out of 10, Exceptional, (6)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is £240
includes taxes & fees
1 Sept - 2 Sept
Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The price is £254
includes taxes & fees
7 Sept - 8 Sept
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

Sleep Woodstock - 2 Double Beds - Dog Friendly

10.0 out of 10, Exceptional, (1)
"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "
The price is £144
includes taxes & fees
21 Aug - 22 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - Dog Friendly King Suite

10.0 out of 10, Exceptional, (1)
"We had an excellent stay, everything was so clean, the room was well appointed and there was even a little communal area with laundry, kitchen, snacks, and shuffleboard. We would absolutely recommend this motel, it’s a gem! "
The price is £153
includes taxes & fees
21 Aug - 22 Aug
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock Mobility Impaired Accessible Suite

The price is £116
includes taxes & fees
21 Aug - 22 Aug
Sleep Woodstock Mobility Impaired Accessible Suite

A charming 1820's farmhouse

10.0 out of 10, Exceptional, (27)
"this property had a very different feel because it was once an inn, which made it feel like we had the whole inn to ourselves, which was lovely. The place is spotless, everything you could possibly need is there, and it is beautifully decorated."
The price is £1,000
includes taxes & fees
19 Aug - 20 Aug
A charming 1820's farmhouse

The Bridgewater House | Game Room | Hiking | Porch

9.6 out of 10, Exceptional, (7)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
The price is £421
includes taxes & fees
18 Aug - 19 Aug
The Bridgewater House | Game Room | Hiking | Porch

Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

9.8 out of 10, Exceptional, (84)
"We had a great stay at this home for a long weekend skiing at Okemo. "
The price is £294
includes taxes & fees
18 Aug - 19 Aug
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (101)
"This place was great! Convenient and clean. The beds were soooo comfy! We walked to town for groceries and dined out in town. We were there for a concert at Okemo which was just a few minutes away. We planned on hanging out back at the fire. Unfortunately, it rained so we hung out in the warm and inviting living room with a fire in the fireplace!! "
The price is £300
includes taxes & fees
18 Aug - 19 Aug
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Okemo's Back Room - in the heart of the village on the shuttle route!

9.6 out of 10, Exceptional, (14)
"Perfect location. Charming place to stay. Very clean. Great view of the creek."
The price is £258
includes taxes & fees
18 Aug - 19 Aug
Okemo's Back Room - in the heart of the village on the shuttle route!

Briggs Ski House | Group Ski Fun | 6 bdrm 4 bath

10.0 out of 10, Exceptional, (1)
"We booked this for a last minute trip to Okemo and it was perfect for our group. It is only a couple minutes from Okemo base and a couple minutes from the cute downtown and a supermarket and craft beer store. The host was easy to talk to and extremely available, and very friendly and helpful! The house was in great condition, clean, and updated."
The price is £816
includes taxes & fees
18 Aug - 19 Aug
Briggs Ski House | Group Ski Fun | 6 bdrm 4 bath

New Ludlow Village Home with Stunning Okemo Mountain View

10.0 out of 10, Exceptional, (6)
"Beautiful and clean place near Okemo with everything you need. "
The price is £408
includes taxes & fees
18 Aug - 19 Aug
New Ludlow Village Home with Stunning Okemo Mountain View

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is £397
includes taxes & fees
8 Sept - 9 Sept
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Modern Farm House…minutes to Okemo; 2 King beds!

9.6 out of 10, Exceptional, (11)
"We were a few families visiting for a ski weekend. Location was great and the house was clean, updated, and had plenty of space. Only thing we thought was inconvenient was the lack of spare TP! "
The price is £477
includes taxes & fees
27 Aug - 28 Aug
Modern Farm House…minutes to Okemo; 2 King beds!

150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

The price is £1,062
includes taxes & fees
25 Aug - 26 Aug
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

9.8 out of 10, Exceptional, (36)
"Very nice"
The price is £449
includes taxes & fees
31 Aug - 1 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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.
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Top Rutland Hotel Reviews