Search Cottages in Callicoon

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Callicoon cottages

Outdoor dining

Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom
Highland Lake
10.0 out of 10, Exceptional, (33 reviews)
"This property is absolutely beautiful. The check in process was easy and the host was super helpful and sweet! Highly recommend this place."
United States
Christina V.
The price is AED 547
AED 3,083 total
includes taxes & fees
11 Mar - 12 Mar
Lakefront | Sport Courts | HotTub | GameRoom
Outdoor dining

Tiny House Cabin in Livingston Manor, NY

Tiny House Cabin in Livingston Manor, NY
Livingston Manor
6.0 out of 10, (3 reviews)
"Marty was really nice. Property was as advertised, but it was out in the country, which is beautiful, but it was advertised as being in town and it’s not. "
United States
Parker B.
The price is AED 643
AED 806 total
includes taxes & fees
18 Mar - 19 Mar
Tiny House Cabin in Livingston Manor, NY
Exterior

Roscoe Cottage Pet Friendly

Roscoe Cottage Pet Friendly
Roscoe
9.8 out of 10, Exceptional, (19 reviews)
"The cottage is very adorable and a great place if your looking to get away from the city life"
United States
Darwin
The price is AED 783
AED 1,138 total
includes taxes & fees
18 Mar - 19 Mar
Roscoe Cottage Pet Friendly
Property grounds

Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (24 reviews)
"Our family had a lovely time on this charming home. From someone who grew up in the Catskills, this was a wonderful getaway from the usual hustle & bustle life."
United States
Liza G.
The price is AED 542
AED 1,202 total
includes taxes & fees
8 Mar - 9 Mar
Charming 120-year-old farmhouse by the creek
Exterior

Deluxe Duplex • Heart Runs & Ski Runs

Deluxe Duplex • Heart Runs & Ski Runs
Pleasant Mount
The price is AED 617
AED 1,514 total
includes taxes & fees
5 Mar - 6 Mar
Deluxe Duplex • Heart Runs & Ski Runs
Exterior

Equestrian House Suites

Equestrian House Suites
3.0 star property
Pleasant Mount
The price is AED 764
AED 2,214 total
includes taxes & fees
11 Mar - 12 Mar
Equestrian House Suites
Exterior

The Hideout Cottage • The Velvet Slopes of Romance

The Hideout Cottage • The Velvet Slopes of Romance
Pleasant Mount
The price is AED 397
AED 1,109 total
includes taxes & fees
5 Mar - 6 Mar
The Hideout Cottage • The Velvet Slopes of Romance
Exterior

2BR Premium Duplex • The Velvet Slopes of Romance

2BR Premium Duplex • The Velvet Slopes of Romance
Pleasant Mount
9.0 out of 10, Wonderful, (2 reviews)
"Would've liked to have more to cook with than just a microwave, other than that the stay was commendable."
United States
Jeremy
The price is AED 463
AED 1,307 total
includes taxes & fees
5 Mar - 6 Mar
2BR Premium Duplex • The Velvet Slopes of Romance
Outdoor dining

Vacation Cottage Getaway • Crystal Peaks, Timeless Love

Vacation Cottage Getaway • Crystal Peaks, Timeless Love
Pleasant Mount
The price is AED 397
AED 1,109 total
includes taxes & fees
5 Mar - 6 Mar
Vacation Cottage Getaway • Crystal Peaks, Timeless Love
Exterior

Forest Hideout Cottage • Valentine’s Grandeur in the Mountains

Forest Hideout Cottage • Valentine’s Grandeur in the Mountains
Pleasant Mount
10.0 out of 10, Exceptional, (1 review)
"the stay was fine, never knew there was a heated pool"
United States
Aliyah A.
Forest Hideout Cottage • Valentine’s Grandeur in the Mountains
Exterior

Countryside Retreat Near Ski Slopes

Countryside Retreat Near Ski Slopes
Pleasant Mount
Countryside Retreat Near Ski Slopes
Exterior

Country Escape • Near Camps & Ski

Country Escape • Near Camps & Ski
Pleasant Mount
Country Escape • Near Camps & Ski
Exterior

Family Cottage and Suite • Country Cottage Close to Ski Mountain

Family Cottage and Suite • Country Cottage Close to Ski Mountain
Pleasant Mount
Family Cottage and Suite • Country Cottage Close to Ski Mountain
Exterior

City Escape • Close to Camps & ELK Ski

City Escape • Close to Camps & ELK Ski
Pleasant Mount
The price is AED 727
AED 1,936 total
includes taxes & fees
5 Mar - 6 Mar
City Escape • Close to Camps & ELK Ski
Exterior

Cottage and Suite • Perfect Stay Close to Ski Slopes

Cottage and Suite • Perfect Stay Close to Ski Slopes
Pleasant Mount
The price is AED 727
AED 1,944 total
includes taxes & fees
18 Mar - 19 Mar
Cottage and Suite • Perfect Stay Close to Ski Slopes
Exterior

Woodland Hideout • Romantic Escape Close to Ski Trails

Woodland Hideout • Romantic Escape Close to Ski Trails
Pleasant Mount
The price is AED 727
AED 1,936 total
includes taxes & fees
18 Mar - 19 Mar
Woodland Hideout • Romantic Escape Close to Ski Trails
Exterior

Family Cottage Escape • Group‑Friendly Retreat Close to Skiing

Family Cottage Escape • Group‑Friendly Retreat Close to Skiing
Pleasant Mount
The price is AED 727
AED 1,936 total
includes taxes & fees
18 Mar - 19 Mar
Family Cottage Escape • Group‑Friendly Retreat Close to Skiing
Exterior

Premier Cottages & Suite • Cozy Cottage Near Ski Mountain

Premier Cottages & Suite • Cozy Cottage Near Ski Mountain
Pleasant Mount
Premier Cottages & Suite • Cozy Cottage Near Ski Mountain
Exterior

Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes

Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes
Pleasant Mount
Family Suites •Close to Ski Runs Near Elk Mountain Ski Slopes
Exterior

Premium Cottages and Suites • Mountain Retreat Near Ski Slopes

Premium Cottages and Suites • Mountain Retreat Near Ski Slopes
Pleasant Mount
Premium Cottages and Suites • Mountain Retreat Near Ski Slopes
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.
View all properties

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Callicoon Hotel Reviews

Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres

10/10 Excellent
"Great little cabin in a great location. "
Michael M. 1-night trip
Posted 1 day ago
Handcrafted Riverfront Cabin on 10 acres

Frequently asked questions

Why book your cottage in Callicoon with Expedia?
Expedia has some terrific cottages in Callicoon, so get set for a memorable vacation on nature's doorstep. If you have a certain budget, choose how much you're willing to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a hot tub or free WiFi. We'll help you find the right digs whatever your plans or bank balance.
How can I find cheap cottages in Callicoon?
With Expedia's useful filter tool, getting your hands on cheap cottages in Callicoon has never been simpler. To discover properties that'll make your wallet happy, narrow your search by amenities, star rating and budget.