Middletown Springs Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middletown Springs vacation rentals

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)
"Our stay was perfectly pleasant but the parking was far from the unit and the ski school and daycare was on a different part of the mountain which made the location inconvenient for having little kids with us."
United States
Teresa W.
$230 nightly
The price is $259
May 26 - May 27
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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.
$168 nightly
The price is $188
May 25 - May 26
Total with taxes and fees
Cozy Rutland Retreat

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
$197 nightly
The price is $223
May 26 - May 27
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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.
$286 nightly
The price is $323
May 25 - May 26
Total with taxes and fees
Cozy Bromley Retreat

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.
$371 nightly
The price is $419
May 26 - May 27
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

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.
$205 nightly
The price is $230
May 24 - May 25
Total with taxes and fees
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

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.
$338 nightly
The price is $382
May 26 - May 27
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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.
$247 nightly
The price is $279
May 26 - May 27
Total with taxes and fees
Comfortable mountain gem with pool, mountain views, & indoor parking space

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.
$579 nightly
The price is $654
May 26 - May 27
Total with taxes and fees
The Tower House | Hot Tub | Firepit | Dog-Friendly

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
$240 nightly
The price is $265
May 24 - May 25
Total with taxes and fees
Okemo | Studio Condo + Loft | Near Slopes + Pool

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.
$308 nightly
The price is $348
May 26 - May 27
Total with taxes and fees
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.
$600 nightly
The price is $678
May 26 - May 27
Total with taxes and fees
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

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.
$241 nightly
The price is $272
May 25 - May 26
Total with taxes and fees
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

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.
$313 nightly
The price is $343
May 26 - May 27
Total with taxes and fees
Killington Condo: Walk to Mountain, Pool & Hot Tub

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.
$343 nightly
The price is $388
May 26 - May 27
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

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)
"We had a wondetful time! Thank you! The hosts were so accommodating and the place is the perfect winter wonderland getaway. "
United States
Gabriele K.
$430 nightly
The price is $482
May 23 - May 24
Total with taxes and fees
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

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.
$241 nightly
The price is $272
May 25 - May 26
Total with taxes and fees
CozyDen - AC, Grill, Bike to Mountain, Porch!

Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (59 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.
$377 nightly
The price is $423
May 26 - May 27
Total with taxes and fees
Quaint, friendly cottage with lakefront location & water views

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.
$259 nightly
The price is $292
May 26 - May 27
Total with taxes and fees
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.
$145 nightly
The price is $157
May 24 - May 25
Total with taxes and fees
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Springs Hotel Reviews

Find out more about Middletown Springs

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

Middletown Springs vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middletown Springs 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 $266 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 Middletown Springs rentals

At Expedia, we put the best Middletown Springs 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 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 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 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 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?

Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen: Visitors like this Middletown Springs vacation home rental. It is located on a lake and has a fireplace, a balcony, 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.