Photo by Swetha Srinivasan

Search Cottages in Ashland

Start date: Check-in selected.
To Date
End date: Check-out
    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
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Cottages in Ashland

Cozy Pet Friendly House Next To Train
Exterior

Cozy Pet Friendly House Next To Train

2.0 star property
6.8 out of 10, (5)
"My family and I stayed here for 5 days in August and it was lovely! Thanks for everything. The beds were very comfortable and the house was very clean and nice."
Cozy Pet Friendly House Next To Train
Charming single family Cottage, pet friendly w fenced in yard,
Exterior

Charming single family Cottage, pet friendly w fenced in yard,

2.0 star property
10.0 out of 10, Exceptional, (17)
"I stayed with my dog for 1 night and the listing was just as described. "
The price is SAR 409
SAR 729 total
includes taxes & fees
5 Oct - 6 Oct
Charming single family Cottage, pet friendly w fenced in yard,
Worcester Home on Indian Lake w/ Shared Boat Dock!
House (3 Bedrooms) | Interior

Worcester Home on Indian Lake w/ Shared Boat Dock!

3.0 star property
8.0 out of 10, Very Good, (1)
Worcester Home on Indian Lake w/ Shared Boat Dock!
Beautiful & Historic Cottage, Steps to Elm Park
Cottage (2 Bedrooms) | Interior

Beautiful & Historic Cottage, Steps to Elm Park

3.0 star property
Beautiful & Historic Cottage, Steps to Elm Park
Trail Access On-site: Gorgeous MCM Deck House!
House (4 Bedrooms) | Interior

Trail Access On-site: Gorgeous MCM Deck House!

3.0 star property
Trail Access On-site: Gorgeous MCM Deck House!
Stunning Sterling Sanctuary: Unwind on the Water!
House (3 Bedrooms) | Interior

Stunning Sterling Sanctuary: Unwind on the Water!

3.0 star property
Stunning Sterling Sanctuary: Unwind on the Water!
Bright & Pet-friendly Home: 2 Mi to Harvard Square
Exterior

Bright & Pet-friendly Home: 2 Mi to Harvard Square

3.0 star property
10.0 out of 10, Exceptional, (1)
Bright & Pet-friendly Home: 2 Mi to Harvard Square
Lakefront Cottage 2 Mi to Palladium in Worcester!
House (2 Bedrooms) | Interior

Lakefront Cottage 2 Mi to Palladium in Worcester!

3.0 star property
Lakefront Cottage 2 Mi to Palladium in Worcester!
Home Near Skiing & Downtown Worcester
House (2 Bedrooms) | Interior

Home Near Skiing & Downtown Worcester

3.0 star property
Home Near Skiing & Downtown Worcester
Vibrant Sterling Lakefront Lodge w/ Kayaks
House (3 Bedrooms) | Interior

Vibrant Sterling Lakefront Lodge w/ Kayaks

3.0 star property
Vibrant Sterling Lakefront Lodge w/ Kayaks
Peaceful Getaway Cottage on grounds of historic mid-century gem
Exterior

Peaceful Getaway Cottage on grounds of historic mid-century gem

3.0 star property
Peaceful Getaway Cottage on grounds of historic mid-century gem
Football Fans Lake Retreat - 5 Mins to Gillette!
House (3 Bedrooms) | Interior

Football Fans Lake Retreat - 5 Mins to Gillette!

3.0 star property
Football Fans Lake Retreat - 5 Mins to Gillette!
Belmont Home < 3 Mi to Harvard Square!
House (3 Bedrooms) | Interior

Belmont Home < 3 Mi to Harvard Square!

3.0 star property
Belmont Home < 3 Mi to Harvard Square!
Beautiful Lakeside Milford Family Home & Deck
Outdoor dining

Beautiful Lakeside Milford Family Home & Deck

3.0 star property
Beautiful Lakeside Milford Family Home & Deck
Great little cottage sitting behind the main house on 4 acres of property.
Property grounds

Great little cottage sitting behind the main house on 4 acres of property.

Great little cottage sitting behind the main house on 4 acres of property.
2 Mi to Gillette Stadium: Foxborough Retreat!
House (4 Bedrooms) | Interior

2 Mi to Gillette Stadium: Foxborough Retreat!

3.0 star property
2 Mi to Gillette Stadium: Foxborough Retreat!
Grand Worcester Getaway w/ Large Private Yard!
House (3 Bedrooms) | Interior

Grand Worcester Getaway w/ Large Private Yard!

3.0 star property
Grand Worcester Getaway w/ Large Private Yard!
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

10/10 Excellent
"Clean room, small but good enough for a single traveler. nice s"
Raquel 1-night trip
Posted 23 hours ago
Copley Square Hotel, a FOUND Hotel

Frequently asked questions

Why book your cottage in Ashland with Expedia?
We think that a vacation should be hassle-free, so if you're looking for cottages in Ashland at an affordable price, Expedia has got your back. Save those pennies and opt for a low-cost option surrounded by nature, or splurge on a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Ashland?
A good way to compare cheap cottages in Ashland is with Expedia's filter tool. Refine your search results by budget, star rating and amenities to secure awesome bargains in just a few keystrokes.