Photo by RoadTrip NewEngland

Search Roxbury Cottage 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

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Roxbury

Mountain Views & Brook Access: Home in Arkville!
Interior

Mountain Views & Brook Access: Home in Arkville!

3.0 star property
Mountain Views & Brook Access: Home in Arkville!
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
Interior

Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great time during our stay. The house was nicely setup. We would go back again."
Cabin 4 Mi to Belleayre Mountain: Ski, Hike & Fish
Catskills Mtn Retreat w/ Panoramic View & Fire Pit
Interior

Catskills Mtn Retreat w/ Panoramic View & Fire Pit

3.0 star property
Catskills Mtn Retreat w/ Panoramic View & Fire Pit
Catskills Home, 5 Mins to Windham Mtn Resort!
Interior

Catskills Home, 5 Mins to Windham Mtn Resort!

3.0 star property
10.0 out of 10, Exceptional, (4)
"This place was awesome. Very clean, nicely appointed, very welcoming. Highly recommend and would definitely stay again. Only downside is that it is a second floor unit and the stairs are a little steep but still totally worth it "
Catskills Home, 5 Mins to Windham Mtn Resort!
Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!
Interior

Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!

3.0 star property
Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!
Private 7-acre Retreat: On-site Pond, Streams
Interior

Private 7-acre Retreat: On-site Pond, Streams

3.0 star property
Private 7-acre Retreat: On-site Pond, Streams
Grand Windham Retreat w/ Fire Pit & Game Room
Interior

Grand Windham Retreat w/ Fire Pit & Game Room

3.0 star property
Grand Windham Retreat w/ Fire Pit & Game Room
Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort
Interior

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

3.0 star property
Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort
Retreat w/ Deck & Grill: 1 Mi to Hunter Mtn Resort
Interior

Retreat w/ Deck & Grill: 1 Mi to Hunter Mtn Resort

3.0 star property
Retreat w/ Deck & Grill: 1 Mi to Hunter Mtn Resort
Scenic Catskills Cabin Rental w/ Hot Tub & Views!
Interior

Scenic Catskills Cabin Rental w/ Hot Tub & Views!

3.0 star property
Scenic Catskills Cabin Rental w/ Hot Tub & Views!
9 Mi to Skiing: Catskills Casita w/ Mountain Views
Interior

9 Mi to Skiing: Catskills Casita w/ Mountain Views

3.0 star property
2.0 out of 10, (1)
"Booked a stay for a group I work with, they arrived to the home at 11:30pm to find out that the booking had been cancelled due to a declined payment but the bank confirmed that the card was good. I did not receive any notification from the managing company that there was a issue so we could not remedy it. I called them, they told me I would've received an email from Expedia (never did), spoke with Hotels.com who reached out and was told the same thing. At the same time, I received two duplicate...
9 Mi to Skiing: Catskills Casita w/ Mountain Views
Andes Vacation Rental w/ Deck & Grill!
Front of property

Andes Vacation Rental w/ Deck & Grill!

3.0 star property
Andes Vacation Rental w/ Deck & Grill!
High Peak Heaven: Cozy Log Cabin on 1 Acre!
Interior

High Peak Heaven: Cozy Log Cabin on 1 Acre!

3.0 star property
High Peak Heaven: Cozy Log Cabin on 1 Acre!
Walk to Ski Lift! Charming Hunter A-frame
Interior

Walk to Ski Lift! Charming Hunter A-frame

3.0 star property
7.6 out of 10, Good, (4)
"A cozy place to spend the weekend"
Walk to Ski Lift! Charming Hunter A-frame
Catskills Mountain Cabin in Bloomville!
Interior

Catskills Mountain Cabin in Bloomville!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful and cozy home Peaceful scenery PERFECT fit for our large families "
Catskills Mountain Cabin in Bloomville!
Renovated Catskills Farmhouse w/ Game Room!
Interior

Renovated Catskills Farmhouse w/ Game Room!

3.0 star property
Renovated Catskills Farmhouse w/ Game Room!
Creekside Catskills Getaway Near Hunter Mountain
Interior

Creekside Catskills Getaway Near Hunter Mountain

3.0 star property
Creekside Catskills Getaway Near Hunter Mountain
'bearpen Lodge' on 125 Acres - Near Belleayre Mtn!
Interior

'bearpen Lodge' on 125 Acres - Near Belleayre Mtn!

3.0 star property
'bearpen Lodge' on 125 Acres - Near Belleayre Mtn!
Hunter Hideaway w/ Yard & Deck: 3 Mi to Ski Slopes
Interior

Hunter Hideaway w/ Yard & Deck: 3 Mi to Ski Slopes

3.0 star property
10.0 out of 10, Exceptional, (1)
Hunter Hideaway w/ Yard & Deck: 3 Mi to Ski Slopes
Vacation Rental Home ~ 2 Mi to Windham Mountain!
Interior

Vacation Rental Home ~ 2 Mi to Windham Mountain!

3.0 star property
Vacation Rental Home ~ 2 Mi to Windham Mountain!
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 Roxbury Hotel Reviews

Urban Cowboy Lodge

Urban Cowboy Lodge

10/10 Excellent
"The staff here was amazing, had a great one night getaway and I wished we stayed longer! Definitely would come back! Service A plus! Food A plus! Scenery outstanding! Definitely recommend for a good wind down from ones busy day to day."
Calvin 1-night trip
Posted 5 hours ago
Urban Cowboy Lodge

Frequently asked questions

Why book your cottage in Roxbury with Expedia?
Booking a cottage in Roxbury is as easy as clicking on your travel dates and choosing an ideal place for outdoor recreation and relaxation. From ritzy retreats to budget-friendly properties and cottages that feature perks like a pool, Expedia has something for all styles. As for terrific deals? We've got them too!
How can I find cheap cottages in Roxbury?
Expedia is here to help you easily source cheap cottages in Roxbury. To reserve your ideal stay in a few quick clicks, use the filter tool to tailor your search results by amenities, star rating and budget.
What is there to do in Roxbury near my cottage?
After you've unpacked your things and settled in, head out and explore the incredible things Roxbury has for you to experience. Plattekill Mountain is a popular attraction to add to your must-see list.