Middletown Springs Holiday Rentals

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Our top choices for Middletown Springs holiday rentals

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)
"Great property, clean and close to the slope"
United States
tiliger01
The price is AU$309
includes taxes & fees
19 May - 20 May
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is AU$529
includes taxes & fees
16 May - 17 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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)
"Location location location!"
United States
Britt H.
The price is AU$570
includes taxes & fees
14 May - 15 May
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

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
9.0 out of 10, Wonderful, (80 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is AU$355
includes taxes & fees
16 May - 17 May
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is AU$450
includes taxes & fees
14 May - 15 May
Cozy Bromley Retreat

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 AU$333
includes taxes & fees
14 May - 15 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.6 out of 10, Excellent, (37 reviews)
"Property was just as advertised. Shuttle to the mountain is only a short 2-3 ride. The spa area was amazing. "
United States
Quinten M.
The price is AU$383
includes taxes & fees
14 May - 15 May
Comfortable mountain gem with pool, mountain views, & indoor parking space

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, (46 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is AU$474
includes taxes & fees
16 May - 17 May
Resort condo with mountain views, full kitchen, and free WiFi

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
The price is AU$925
includes taxes & fees
17 May - 18 May
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"This condo is a true ski-in, ski-out experience! Literally walked out the back door and skied to the lift. (A/B lifts) The kitchen was well appointed, the bed comfortable, and was perfectly set up for a ski vacation. The entire space had a comfortable, rustic vibe. Would definitely stay here again when returning to Okemo."
United States
Patricia D.
The price is AU$527
includes taxes & fees
14 May - 15 May
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.4 out of 10, Good, (32 reviews)
"Great location."
United States
Dustin S.
The price is AU$400
includes taxes & fees
14 May - 15 May
Welcoming condo near the slopes with free WiFi and full kitchen

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (18 reviews)
"Would stay again!"
United States
Hannah M.
The price is AU$220
includes taxes & fees
14 May - 15 May
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

Okemo | Studio Condo + Loft | Near Slopes + Pool

Okemo | Studio Condo + Loft | Near Slopes + Pool
Jackson Gore Base Area
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is AU$361
includes taxes & fees
14 May - 15 May
Okemo | Studio Condo + Loft | Near Slopes + Pool

Killington Condo: Walk to Mountain, Pool & Hot Tub

Killington Condo: Walk to Mountain, Pool & Hot Tub
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent VRBO. Perfect location to the mountain. Condo was modern and clean and very comfortable. Would go back again!! "
United States
Sheri L.
The price is AU$469
includes taxes & fees
14 May - 15 May
Killington Condo: Walk to Mountain, Pool & Hot Tub

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, (41 reviews)
"Very easy check in and out and clean home. Streets nearby can be hard to travel without 4 wheel drive. "
United States
Andrew O.
The price is AU$667
includes taxes & fees
21 May - 22 May
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is AU$971
includes taxes & fees
14 May - 15 May
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is AU$375
includes taxes & fees
18 May - 19 May
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is AU$260
includes taxes & fees
15 May - 16 May
Cozy Rutland Retreat

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AU$893
includes taxes & fees
14 May - 15 May
The Tower House | Hot Tub | Firepit | Dog-Friendly

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AU$375
includes taxes & fees
14 May - 15 May
CozyDen - AC, Grill, Bike to Mountain, Porch!
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

Find out more about Middletown Springs

Everything you need to know about Middletown Springs holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown Springs holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Middletown Springs holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middletown Springs holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown Springs. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown Springs holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown Springs holiday rentals we have selected for you start as low as AU$375 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown Springs rentals

At Expedia, we put the best Middletown Springs holiday 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 Middletown Springs 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 Middletown Springs holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown Springs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Middletown Springs?

Yes, there are holiday rentals close to the most popular sights in Middletown Springs, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middletown Springs has to offer?

Okemo Mountain Lodging by Vail Resorts: This holiday home rental outside of Middletown Springs is in the mountains and offers an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

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 wider area, you’ll find Middletown Springs Public Library and Lake Saint Catherine State Park.

What are holiday rentals like in Middletown Springs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown Springs. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips.