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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Featured Cottages in Middletown and around

Our top choices for Middletown cottages

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
The price is €261
includes taxes & fees
30 Sept - 1 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Charming Cottage in the Heart of the Shawangunks
Exterior

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (15)
"The gatehouse was a perfect spot for a girls trip getaway. Secluded enough, but close to some local activities and restaurants! Cozy vibe and place had everything we needed!"
Charming Cottage in the Heart of the Shawangunks
Charming 2-bedroom cottage in delightful Eldred with WiFi
Exterior

Charming 2-bedroom cottage in delightful Eldred with WiFi

9.0 out of 10, Wonderful, (2)
"The cottage was cute, but the pool was the selling point. "
Charming 2-bedroom cottage in delightful Eldred with WiFi
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Terrace/patio

SwimSpa | Lake | Fish | Kayak | Hike | Firepit

9.6 out of 10, Exceptional, (5)
"Enjoyed our stay very much! Would highly recommend for someone seeking a nice quite get-away. Very nice Swim-spa for relaxation, many board games. We look forward to returning!"
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Scenic Hudson Valley Getaway • Farms & Vineyards
Exterior

Scenic Hudson Valley Getaway • Farms & Vineyards

10.0 out of 10, Exceptional, (1)
"It was exactly what my family and I needed. A cozy, quiet place to stay with mountain views. The owner is responsive and communicates quickly. Will come back again."
Scenic Hudson Valley Getaway • Farms & Vineyards
Cozy Cottage with Woodstock Scavenger Hunt
Terrace/patio

Cozy Cottage with Woodstock Scavenger Hunt

10.0 out of 10, Exceptional, (4)
"Great house, plenty of space, nice deck; beautiful property!Great little neighborhood. The hostess is so nice and helpful! I plan on coming back next year for a longer stay!"
The price is €239
includes taxes & fees
21 Sept - 22 Sept
Cozy Cottage with Woodstock Scavenger Hunt
Lazy River Cottage on the Delaware River
Property grounds

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (157)
"We had a wonderful relaxing time!!"
Lazy River Cottage on the Delaware River
Hike & Fish: Outdoor Retreat Near Trails
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
The price is €255
includes taxes & fees
30 Sept - 1 Oct
Hike & Fish: Outdoor Retreat Near Trails
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Exterior

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (103)
"Our 3rd time staying here. Fits our need perfectly. Great host nice home. Couldn't ask for anything more. Definitely will be back."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Hike, Fish, Ski & More: Spacious Gem in Catskills!
House (4 Bedrooms) | Interior

Hike, Fish, Ski & More: Spacious Gem in Catskills!

3.0 star property
Hike, Fish, Ski & More: Spacious Gem in Catskills!
6 Mi to Bethel Woods: Cabin w/ Pool Access
House (1 Bedroom) | Interior

6 Mi to Bethel Woods: Cabin w/ Pool Access

3.0 star property
6 Mi to Bethel Woods: Cabin w/ Pool Access
5 Mi to Marina & Raceways: Mongaup Valley Retreat!
House (2 Bedrooms) | Interior

5 Mi to Marina & Raceways: Mongaup Valley Retreat!

3.0 star property
5 Mi to Marina & Raceways: Mongaup Valley Retreat!
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Property grounds

Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

9.6 out of 10, Exceptional, (39)
"I spent a weekend with my sister and had a glorious time. The house is cleverly designed with everything you need for a comfortable stay. But who wants to even stay inside with such a glorious river expanse at your footsteps. Wonder was friendly, helpful and responsive. We’d stay again in a heartbeat!"
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Luxe Family Home on Orange Lake w/ Private Dock!
House (3 Bedrooms) | Interior

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property
Luxe Family Home on Orange Lake w/ Private Dock!
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Outdoor spa tub

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

10.0 out of 10, Exceptional, (33)
"We could not have better things to say about our stay. The place is amazing and close to plenty of fun activities. It offered the perfect balance of nature, fun, and relaxation. Communication from the hosts was excellent and clear."
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

The price is €186
includes taxes & fees
23 Sept - 24 Sept
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Charming Victorian Retreat w/ Hudson River Views
House (3 Bedrooms) | Interior

Charming Victorian Retreat w/ Hudson River Views

3.0 star property
Charming Victorian Retreat w/ Hudson River Views
Hello Small Stone
Exterior

Hello Small Stone

9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
The price is €379
includes taxes & fees
1 Oct - 2 Oct
Hello Small Stone
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Exterior

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

10.0 out of 10, Exceptional, (10)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
The price is €238
includes taxes & fees
24 Sept - 25 Sept
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
Terrace/patio

2 Lake Cabins | Pool+HotTub | Game Room | 23acs

10.0 out of 10, Exceptional, (2)
"Gorgeous property for a family reunion. Host was very accommodating and responsive. Lots of fun amenities and room for everyone to spread out. Great open space on the lake but still felt private and quiet. Wifi throughout entire property. Absolutely recommend and would definitely book again."
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
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 Hotel Reviews

Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

10/10 Excellent
"Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect weekend getaway. Will definitely stay again, either with a group or just the 2 of us."
David 1-night trip
Posted 2 days ago
Wildflower Farms, Auberge Resorts Collection

Find out more about Middletown

Find out more about Middletown

Middletown Cottages information

Number of reviews
456
Accommodation
142 Cottages
Lowest Price
€186
Highest Price
€379

Frequently asked questions

Why book your cottage in Middletown with Expedia?
We think a getaway should be a walk in the park, so if you're seeking cottages in Middletown at a competitive rate, Expedia has got your back. Keep costs down and select an inexpensive option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Middletown?
With Expedia's useful filter tool, sourcing cheap cottages in Middletown is a cinch. To discover accommodation that'll make your wallet smile, narrow down your search by budget, amenities and star rating.
What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.

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Explore a world of travel with Expedia