Middletown Springs Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Middletown Springs Vacation Homes

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Enjoy cooking in this well-equipped kitchen with a wooden dining table and chairs.

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

8.2 out of 10, Very good, (39)
"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 😂
Enjoy a serene lake view from this deck with a round table and comfortable bench.

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.
Cozy cabin nestled among trees, surrounded by a crackling campfire.

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

10.0 out of 10, Exceptional, (89)
"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!
Relax in this inviting living room with a stunning mountain view, comfortable couch, and warm table setting.

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
Enjoy cooking in this well-equipped kitchen with a large island, bar stools, and stainless steel appliances.

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

10.0 out of 10, Exceptional, (59)
"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
Relax in a hot tub surrounded by serene winter scenery.

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
Relax by the pool surrounded by comfortable seating and lush greenery.

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

8.4 out of 10, Very good, (42)
"Great place"
Recently updated home with shared hot tub, pool, and easy ski access
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
Stunning two-story home with a charming red door and cozy porch.

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

10.0 out of 10, Exceptional, (46)
"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
Enjoy meals and gatherings in this kitchen with a central island, dining area, and large window offering a view of the surrounding landscape.

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
Situated in a secluded wooded area, this cabin offers a traditional two-story retreat with a balcony and multiple windows.

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
Set amidst a serene natural landscape, this lodge features a multi-level structure with a distinctive roof and spacious balconies.

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

9.8 out of 10, Exceptional, (173)
"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!
Stroll through the beautifully maintained garden, surrounded by lush plants and a serene natural setting.

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
Relax on the porch with a bench and table, surrounded by a potted plant and a cozy atmosphere.

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
Escape to a serene forest retreat surrounded by tall pine trees and a peaceful atmosphere.

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 $143
CA $216 total
includes taxes & fees
Aug 10 - Aug 11
104 Two Queen Bed Standard Hotel Room outdoor heated pool
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.
Relax on the covered porch with comfortable seating and a scenic view of the surrounding mountains and trees.

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

9.8 out of 10, Exceptional, (16)
"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
Escape to STRUC GLEN, a cozy cabin nestled among evergreen trees, offering a serene winter retreat.

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

9.2 out of 10, Wonderful, (37)
"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
Cozy living room with a stone fireplace, American flag, and comfortable seating.

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 $227
CA $700 total
includes taxes & fees
Aug 10 - Aug 11
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.
Enjoy cooking in this well-equipped kitchen with a central island, sink, and stove, surrounded by ample dining space.

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

9.0 out of 10, Wonderful, (4)
"Big and spacious. "
The price is CA $272
CA $830 total
includes taxes & fees
Aug 10 - Aug 11
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!
A single-story house with a gabled roof and chimney sits in a winter landscape.

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

10.0 out of 10, Exceptional, (4)
"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.
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Top Middletown Springs Hotel Reviews

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"My husband and I stayed one night to celebrate our anniversary. The room was clean, roomy and comfortable. The hotel is huge in a beautiful surrounding with many activities included in the price. Swimming, bike riding and an easy drive into the main town. We would recommend the Equinox and plan on returning in the future for several nights."
Roberta 1-night trip
Posted 2 days ago
The Equinox Golf Resort & Spa