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Ludlow vacation rentals

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Top-rated vacation rentals in Ludlow

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Barn in Andover

4.98 out of 5 average rating, 119 reviews

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Condo in Ludlow

4.94 out of 5 average rating, 108 reviews

Lovely 1-Bedroom condo with indoor fireplace!

This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, gifts, restaurants and bars. It even has a tap house, "Eight Oh Brew" on the base floor of the building, down just 2 flights of stairs from where you will be staying. This location has onsite parking, laundry and firewood.

Condo in Ludlow

4.92 out of 5 average rating, 130 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

Guesthouse in Wallingford

4.98 out of 5 average rating, 639 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Barn in Chester

4.99 out of 5 average rating, 575 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Cottage in Windsor

4.97 out of 5 average rating, 368 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Rental unit in Weathersfield

4.99 out of 5 average rating, 171 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Cabin in Mount Holly

4.87 out of 5 average rating, 104 reviews

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

Condo in Ludlow

4.91 out of 5 average rating, 125 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Home in Ludlow

4.97 out of 5 average rating, 151 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Much of the house newly renovated in the Fall, 2023. Relax in this 3-level (1700+ sq. ft) ski chalet that's a 4 min drive to the Okemo Mountain Resort and the center of town, and a 6 min drive to Jackson Gore. Take in the 180-degree views of your wooded backyard with floor-to-ceiling windows and unwind in front of the fireplace or relax in the Jacuzzi hot tub in your private oasis on the mountain.

Loft in Ludlow

4.95 out of 5 average rating, 774 reviews

Spacious Renovated Barn Apt on 100 acres!

Our clean unique hideaway is only two miles from many restaurants, cute shops, the gorgeous Buttermilk Falls and Okemo Mountain Resort where you can enjoy mountain biking, a ropes course or skiing and riding! Enjoy 100 acres of hiking right outside your door. There is nice fire fire pit, hot tub and outdoor seating. Perfect location for the outdoor enthusiast or a relaxing weekend in cool VT air!

Rental unit in Andover

4.98 out of 5 average rating, 409 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Vacation rentals for every style

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Apartments

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Popular amenities for Ludlow vacation rentals

Laptop-friendly workspace

Stay near Ludlow's top sights

Jackson Gore Inn at Okemo Mountain Resort16 locals recommend

Okemo station5 locals recommend

Shaw's133 locals recommend

Killarney74 locals recommend

The Hatchery61 locals recommend

Mr. Darcy's Bar & Grill48 locals recommend

House rentals in Ludlow

Home in Barnard

4.98 out of 5 average rating, 126 reviews

The Looking Glass, a modernistic escape

Home in Londonderry

4.98 out of 5 average rating, 115 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

Home in Danby

4.96 out of 5 average rating, 215 reviews

Comfortable farmhouse with stunning views

Home in Clarendon

4.96 out of 5 average rating, 270 reviews

Custom 2BR Vacation Retreat in Killington Valley!

Home in West Windsor

4.98 out of 5 average rating, 185 reviews

Meadow View. 35 acres outside your door!

Home in Poultney

4.93 out of 5 average rating, 102 reviews

Cozy Home in Poultney, Vermont.

Home in Weston

4.95 out of 5 average rating, 218 reviews

Weston Farmhouse-Clean, Fast WiFi, Generator!

Home in Weston

4.96 out of 5 average rating, 249 reviews

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Condo rentals in Ludlow

Condo in Killington

4.94 out of 5 average rating, 155 reviews

Renovated unit, prime location! Shuttle on/Ski off

Condo in Killington

4.94 out of 5 average rating, 161 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Condo in Ludlow

4.95 out of 5 average rating, 110 reviews

Slopeside condo at the base of Okemo-steps to lift

Condo in Killington

4.94 out of 5 average rating, 233 reviews

Dog-Friendly 2BD/2BA Oasis - Pool, Hot Tub & Spa

Condo in Plymouth

4.91 out of 5 average rating, 138 reviews

Canyons Unit:Hot Tub,two mile to Skyeship Gondolas

Condo in Killington

4.93 out of 5 average rating, 183 reviews

Newly renovated ski retreat at Killington

Condo in Stratton

4.96 out of 5 average rating, 129 reviews

Cozy condo within walking distance to the slopes.

Condo in Killington

4.78 out of 5 average rating, 287 reviews

Serene Top Floor Condo (resort style amenities)

Other great vacation rentals in Ludlow

Cabin in Ludlow

4.97 out of 5 average rating, 29 reviews

Cozy Summer Cabin | Peaceful Backyard and BBQ

Condo in Ludlow

5 out of 5 average rating, 24 reviews

2 BR/2BA Ski In/Ski Out Condo on Okemo- Sleeps 6

Rental unit in Ludlow

4.97 out of 5 average rating, 31 reviews

Okemo Mountain Retreat

Home in Ludlow

5 out of 5 average rating, 89 reviews

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home

Condo in Ludlow

4.91 out of 5 average rating, 85 reviews

One Bedroom Suite Near Okemo

Home in Mount Holly

4.96 out of 5 average rating, 51 reviews

Modern VT Farmhouse w/Hot Tub - 10 mins to Okemo

Home in Ludlow

5 out of 5 average rating, 27 reviews

AFrame w/ lake ~ 5min to Okemo ~ 15 to Killington

Home in Ludlow

5 out of 5 average rating, 30 reviews

Mountain House & Private Hot Tub

Quick stats about vacation rentals in Ludlow

Total rentals
160 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
5.3K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Ludlow?
Yes! Work meets play with ease at over 70 vacation rentals in Ludlow featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Ludlow?
Four-legged friends are welcome in Ludlow. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in condo rentals in Ludlow?
Experience the best of Ludlow with our condo rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do condo rentals in Ludlow have wifi?
Absolutely! We offer over 30 condo rentals with wifi in Ludlow. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Ludlow have self check-in?
Absolutely! We offer over 10 condo rentals with self check-in in Ludlow. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly condo rentals in Ludlow?
Ludlow has more than 20 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Ludlow have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Ludlow. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Condo Rentals in Ludlow?
Enhance your stay in our Condo Rentals with the most popular amenities: over 30 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

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