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Middletown Springs Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middletown Springs vacation rentals

A wooden deck with a white lattice base, a metal roof, and a house with a garage door in the background.

1. Beautiful 1-bedroom cabin with AC in wonderful Wells

Beautiful 1-bedroom cabin with AC in wonderful Wells
Wells
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful location with Mountain views. Property owners were wonderful hosts."
United States
Jane
The price is ￥17,758
￥23,426 total
includes taxes & fees
Oct 4 - Oct 5
Beautiful 1-bedroom cabin with AC in wonderful Wells
A sunroom with a large window, wicker furniture, and a fish mounted on the wall.

2. Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (60 reviews)
"The cottage is in a nice spot on the lake. It is accurately depicted in the listing and was great for our trip"
United States
Jim V.
The price is ￥16,574
￥68,098 total
includes taxes & fees
Oct 9 - Oct 10
Quaint, friendly cottage with lakefront location & water views
A yurt with a red door, a visible interior with a fire, and snow outside.

3. Off-Grid Mongolian Yurt on Vermont Sheep Farm

Off-Grid Mongolian Yurt on Vermont Sheep Farm
Poultney
The price is ￥16,416
￥23,690 total
includes taxes & fees
Nov 2 - Nov 3
Off-Grid Mongolian Yurt on Vermont Sheep Farm
A wooden cabin interior with a wooden dresser, a floral chair, a teal refrigerator, and a shelf with mugs and a coffee maker.

4. Peaceful 1-bedroom bungalow with AC in charming Wells

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
10.0 out of 10, Exceptional, (1 review)
"Clean comfy quiet spot."
United States
Dillon B.
The price is ￥29,123
￥37,393 total
includes taxes & fees
Oct 6 - Oct 7
Peaceful 1-bedroom bungalow with AC in charming Wells
A dining table set with plates, glasses, and a vase with a plant.

5. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is ￥14,364
￥29,480 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Rutland Retreat
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

6. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
The price is ￥21,182
￥65,891 total
includes taxes & fees
Oct 24 - Oct 25
Killington Retreat | Deck-Fire Pit-Mountain Views!
A shower area with dark marble tiles and a pebble-patterned floor.

7. Comfy Cottage with Private Hot Tub in Historic East Poultney

Comfy Cottage with Private Hot Tub in Historic East Poultney
Poultney
10.0 out of 10, Exceptional, (16 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is ￥33,938
￥61,701 total
includes taxes & fees
Oct 14 - Oct 15
Comfy Cottage with Private Hot Tub in Historic East Poultney
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

8. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is ￥14,064
￥36,583 total
includes taxes & fees
Oct 4 - Oct 5
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A two-story house with a covered porch and a gabled roof.

9. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
Fair Haven
9.0 out of 10, Wonderful, (36 reviews)
"Very nice house to stay in Fair Haven VT. Worked perfectly for us and beautiful area. Clean and has everything you need."
United States
Amy G.
The price is ￥21,310
￥47,982 total
includes taxes & fees
Oct 5 - Oct 6
Historic Victorian Estate 4 Bed 2 Bath Fast Wifi
A room with a grey sofa, a wooden cabinet with pictures, and a poster on the wall.

10. Centrally located apartment for the skier & outdoor enthusiast

Centrally located apartment for the skier & outdoor enthusiast
Rutland
The price is ￥20,718
￥53,031 total
includes taxes & fees
Oct 4 - Oct 5
Centrally located apartment for the skier & outdoor enthusiast
A rustic cabin with a wooden porch, a door, and a large potted plant.

11. Unique family-friendly Vermont cabin!

Unique family-friendly Vermont cabin!
Fair Haven
10.0 out of 10, Exceptional, (26 reviews)
"Another great stay."
United States
leonard
The price is ￥28,271
￥48,713 total
includes taxes & fees
Oct 4 - Oct 5
Unique family-friendly Vermont cabin!
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

12. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.2 out of 10, Wonderful, (9 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is ￥27,466
￥75,272 total
includes taxes & fees
Nov 3 - Nov 4
large ski ranch hot tub close to killington pets ok
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

13. Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
The price is ￥11,602
￥45,740 total
includes taxes & fees
Oct 4 - Oct 5
Welcoming condo near the slopes with free WiFi and full kitchen
A modern kitchen with stainless steel appliances, a dining table, and a wooden floor.

14. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails
Rutland
10.0 out of 10, Exceptional, (7 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is ￥32,517
￥65,211 total
includes taxes & fees
Nov 3 - Nov 4
4BR Home | Walk Downtown Rutland + Trails
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

15. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (12 reviews)
"Quick trip but would stay here again"
United States
John O.
The price is ￥23,777
￥64,955 total
includes taxes & fees
Oct 5 - Oct 6
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A residential area with houses, a swimming pool, and a mountain backdrop.

16. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was great"
United States
Nathan H.
The price is ￥15,978
￥46,258 total
includes taxes & fees
Oct 4 - Oct 5
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A living room with a fireplace, a sofa, a coffee table, and a television.

17. Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is ￥14,751
￥59,945 total
includes taxes & fees
Oct 6 - Oct 7
Resort condo with mountain views, full kitchen, and free WiFi
A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

18. Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
Rutland
9.4 out of 10, Exceptional, (6 reviews)
"Perfect spot for a large group to enjoy Rutland, Killington, and the surrounding area. Plenty of beds for everyone, and bathrooms so no one felt cramped whatsoever. Beautiful home and safe neighborhood. All around a great stay. If we come back for the US Open of MTB next year, this house would be high on our list to stay in again."
United States
Matthew T.
Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

19. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is ￥23,777
￥65,312 total
includes taxes & fees
Oct 4 - Oct 5
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

20. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.6 out of 10, Exceptional, (71 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
The price is ￥20,923
￥61,277 total
includes taxes & fees
Oct 5 - Oct 6
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
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 Middletown Springs Hotel Reviews

Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"Great staff service; love their hot breakfast menu order"
Sarah 1-night trip
Posted 2 hours ago
Mountain Sports Inn

Find out more about Middletown Springs

Search for holiday rentals in Middletown Springs on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown Springs using one of the methods below:

  • View our selection of featured holiday rentals in Middletown Springs
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Look no further and take a look at our great range of rental properties in Middletown Springs!

Frequently asked questions

Can I find vacation rentals in Middletown Springs?

Yes, you can find vacation rentals near popular points of interest in Middletown Springs, or you can go with a more secluded option if you're looking for relaxation.

What's the top vacation rental that Middletown Springs has to offer?

Rustic home with a private hot tub, cable, & washer/dryer: You might want to consider this vacation home rental near Middletown Springs, which is located in the city center and has a fireplace, a hot tub, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Middletown Springs?

While exploring the area, visit family-friendly sights like Pond Hill Ranch and Pro Rodeo, or get outside and enjoy nature at Mineral Springs Park. In the larger area, you’ll find Middletown Springs Public Library and Lake Saint Catherine State Park.

What are vacation rentals like in Middletown Springs?

Vacation rentals are privately owned accommodations you can book for several days or longer in Middletown Springs. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for small groups.