Middletown Springs Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Browse Select Middletown Springs Vacation Homes

Our top choices for Middletown Springs vacation homes

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.0 out of 10, Very good, (40)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Water front home with large two tiered deck! 2 bathrooms 😂
Property grounds

Water front home with large two tiered deck! 2 bathrooms 😂

9.4 out of 10, Exceptional, (105)
"My family has stayed here 2 weekends and it was perfect for us. Great location and perfect area to relax. Our dog enjoyed swimming and we enjoyed fishing. Great communication with manager also. Look forward to staying here again!"
Water front home with large two tiered deck! 2 bathrooms 😂
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
Property grounds

Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

10.0 out of 10, Exceptional, (91)
"My family and I loved the stay. Great place to enjoy the nature. The house had everything we needed such as great kitchen, fireplace, and jacuzzi. "
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (72)
"We absolutely LOVED our stay. The house and all its amenities were perfect for our ski trip, and we would be thrilled to come back again some time. "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon
Fridge, microwave, oven, stovetop

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

10.0 out of 10, Exceptional, (60)
"Beautiful house right in the village. Easy access to both Sugarbush and Killington. Would definitely stay here again. "
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon
Alpine 6-BR Estate On Okemo Mountain
Outdoor spa tub

Alpine 6-BR Estate On Okemo Mountain

10.0 out of 10, Exceptional, (2)
"Nice place"
Alpine 6-BR Estate On Okemo Mountain
Recently updated home with shared hot tub, pool, and easy ski access
Indoor pool

Recently updated home with shared hot tub, pool, and easy ski access

8.4 out of 10, Very good, (44)
"Great place"
Recently updated home with shared hot tub, pool, and easy ski access
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
Exterior

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

10.0 out of 10, Exceptional, (47)
"Our family had a great stay in Ludlow for a four day ski vacation. Tom and Patti were great hosts and their home is convenient to both Okemo and Killington. The hosts communicated well with us and their place was perfect for our needs (family of 4), clean, and convenient to downtown Ludlow and restaurants. "
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Fridge, microwave, oven, stovetop

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Exterior

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (36)
"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (174)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Exterior detail

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (63)
"We had a "
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Property grounds

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (25)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
104 Two Queen Bed Standard Hotel Room outdoor heated pool
Property grounds

104 Two Queen Bed Standard Hotel Room outdoor heated pool

8.6 out of 10, Excellent, (27)
"Excellent customer service and beautiful, well-maintained property."
The price is CA $144
CA $218 total
includes taxes & fees
Aug 24 - Aug 25
104 Two Queen Bed Standard Hotel Room outdoor heated pool
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.
Terrace/patio

Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

9.8 out of 10, Exceptional, (17)
"Spacious house and beautiful grounds."
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Property grounds

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (38)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Luxury 4-BR Mountain Estate 10-min to Manchester
Interior

Luxury 4-BR Mountain Estate 10-min to Manchester

2.0 star property
10.0 out of 10, Exceptional, (2)
"This property is amazing: the grounds, the gardens and of course an exceptional, well equipped house. The architecture, the views and the many bedrooms and bathrooms made it so comfortable for our group of nine. The kitchen is well organized and has every convenience for cooking in."
Luxury 4-BR Mountain Estate 10-min to Manchester
The Killington Bungalow: A cozy 2-bedroom retreat in the heart of Killington, Vermont
Fridge, microwave, oven, stovetop

The Killington Bungalow: A cozy 2-bedroom retreat in the heart of Killington, Vermont

The price is CA $232
CA $712 total
includes taxes & fees
Aug 24 - Aug 25
The Killington Bungalow: A cozy 2-bedroom retreat in the heart of Killington, Vermont
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.
Dining

Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.

9.0 out of 10, Wonderful, (4)
"Big and spacious. "
Susan Lane Hideaway: 4BR/3.5BA Renovated Home. Close to skiing and town.
Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!
Exterior

Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!

10.0 out of 10, Exceptional, (6)
"We loved staying at the Sloane School! It was modern yet so cozy. It had everything we needed, there were only three of us but there was plenty of room for more. The hot tub was delightful, the bathrooms were beautiful, the kitchen was so nice and everything was immaculate! I would stay there again in a heartbeat! "
Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!
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
Sign in
Sign up, it's free

Top Middletown Springs Hotel Reviews

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Restaurant could be better"
Krista 1-night trip
Posted 2 days ago
Kimpton Taconic Hotel by IHG