A red two-story building with a porch, labeled "The Vermont Country Store," featuring a sign for "The Orton Family Business."

Weston Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Weston vacation rentals

TV, DVD player

1. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
$204 nightly
The price is $231
Aug 31 - Sep 1
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Children's area

2. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (19 reviews)
"This is an amazing location. The home is exceptionally clean and well equipped. The pool was amazing and so was our experience. We were centrally located to everything we wanted to do. I would highly recommend this home and Management company to anyone visiting the Bromley area. Exceptional."
United States
Jaime
$304 nightly
The price is $343
Aug 31 - Sep 1
Total with taxes and fees
Cozy Bromley Retreat
Property grounds

3. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
$235 nightly
The price is $265
Aug 31 - Sep 1
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
TV

4. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
$383 nightly
The price is $433
Sep 2 - Sep 3
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Interior

5. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (24 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
$482 nightly
The price is $544
Aug 31 - Sep 1
Total with taxes and fees
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Exterior

6. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
$228 nightly
The price is $258
Aug 31 - Sep 1
Total with taxes and fees
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Interior

7. Perfect Getaway! Cozy, Modern & Convenience to Everything!

Perfect Getaway! Cozy, Modern & Convenience to Everything!
Ludlow
9.8 out of 10, Exceptional, (86 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
$160 nightly
The price is $181
Sep 15 - Sep 16
Total with taxes and fees
Perfect Getaway! Cozy, Modern & Convenience to Everything!
Exterior

8. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
$239 nightly
The price is $270
Aug 31 - Sep 1
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Golf

9. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
$204 nightly
The price is $231
Aug 31 - Sep 1
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location
Exterior

10. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
$210 nightly
The price is $238
Aug 31 - Sep 1
Total with taxes and fees
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Exterior

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

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
$201 nightly
The price is $227
Aug 31 - Sep 1
Total with taxes and fees
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Smart TV, fireplace, video games, books

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

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
$438 nightly
The price is $491
Aug 31 - Sep 1
Total with taxes and fees
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Interior

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

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
$230 nightly
The price is $259
Aug 31 - Sep 1
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Terrace/patio

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

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Perfect location. Neat place. Very clean!"
United States
Frank F.
$449 nightly
The price is $507
Sep 2 - Sep 3
Total with taxes and fees
Okemo's Back Room - in the heart of the village on the shuttle route!
Exterior

15. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (171 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
$330 nightly
The price is $370
Aug 31 - Sep 1
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
TV, fireplace, foosball, stereo

16. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
$337 nightly
The price is $361
Sep 2 - Sep 3
Total with taxes and fees
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Outdoor pool, a heated pool

17. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (24 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
$483 nightly
The price is $541
Aug 31 - Sep 1
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Dining

18. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
$352 nightly
The price is $398
Sep 1 - Sep 2
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
Outdoor spa tub

19. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (40 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
$591 nightly
The price is $663
Aug 31 - Sep 1
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Exterior detail

20. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (30 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
$733 nightly
The price is $828
Aug 31 - Sep 1
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
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 Weston Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"There was a lot to love about Holiday Inn Club Vacations Mount Ascutney, especially for a larger family or group. Our three-bedroom villa was BY FAR the largest accommodation of our trip and surprisingly affordable. We had tons of room to spread out, a decent-sized kitchen for cooking, and FREE laundry—a huge win during a long road trip! The villa kitchen was helpful but pretty minimally stocked. Cooking utensils and cutting boards were lacking, so bring some basics if you plan to cook. Grills are available, but you’ll need charcoal. I’d recommend buying it and any groceries before arriving because the onsite marketplace is expensive. The biggest disappointment was the pool, which is closed through 2027. Traveling with kids, that was a major bummer and definitely something families should know before booking. The location is incredibly beautiful, tucked away on a Vermont mountainside, but it is truly in the middle of nowhere. Come prepared! Overall, the incredible amount of space and affordability made it work really well for our group. It wasn’t our favorite stay of the trip, but the value for a three-bedroom villa was hard to beat."
Lindsey 1-night trip
Posted 4 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Weston

Everything you need to know about Weston 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 Weston 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 Weston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Weston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Weston. 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 Weston 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 $231 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 Weston rentals

At Expedia, we put the best Weston 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 Weston 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 Weston 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 Weston. 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

Frequently asked questions

Are there vacation rentals in Weston?

Yes, we offer vacation rentals close to popular attractions in Weston, or you can choose a more secluded option if you're looking for relaxation. Weston is known for its ski areas and entertainment choices. Make sure you have time to check out the theaters and shopping during your trip.

What are some of the best vacation home rentals in Weston?

Birch Lodge - mountain views, hottub, minutes to Okemo!: This vacation home near Weston is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Weston?

Choose from 11 Expedia vacation rentals in Weston for a memorable vacation.

What can I see and do in Weston?

Enjoy the outdoors at Green Mountain National Forest and West River, or simply take in cultural attractions like Weston Playhouse and Mill Museum. In the larger area, you’ll find Weston Priory and Viking Nordic Center.

What are vacation rentals like in Weston?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Weston. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family gatherings.