Vacation rentals in Ashland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Ashland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Apartment in Framingham
Spacious 2 Br with All The Comforts Of Home
This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.
Dec. 24 – 31
$253 CAD per night
4.91 out of 5 average rating, 256 reviews
Guest favourite
Home in Framingham
1BR—Bright & Cozy 2-Level Home — 25 Min to Boston
750sqft One-Bedroom, 2-Level Apartment @ our 3-Rental Property 1st Floor: —Fully Stocked Granite Kitchen w/Dishwasher + Essentials & Cookware —Living Room w/Queen Sofa Bed & Dining Table 2nd Floor: —Bedroom - Queen Memory Foam Bed + Full Length Mirror —Bathroom - Shower/Tub —Desk & Chair + Wardrobe Backyard Patio Laundry Room (Basement) Driveway Parking 25 min to Boston 15 min walk to Train 5 min walk to Jack’s Abby Brewery 3 min walk to Park/Playground Cleaned & Sanitized/COVID Conscious Host
Apr. 2 – 9
$17 CAD per night
4.89 out of 5 average rating, 246 reviews
Guest favourite
Home in Southborough
Luxury Living at its Best in X-Large 8 Beds Estate
The talk & admiration of the neighborhood. Airbnb Guests’ Favorite with over 130+ 5 Star Reviews. When you book, we aim to deliver everything that is described in order to earn the same 5 stars all around review from you. This large expansive 8 bedrooms, 4.5 baths estate home has had a complete renovation adding today’s high end touches, yet preserving old world charm. You will experience modern amenities, a massive kitchen & luxury living in a large open space. SORRY: We do not allow parties.
Feb. 8 – 15
$912 CAD per night
4.9 out of 5 average rating, 136 reviews

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Ashland Ale House5 locals recommend
Stone's Public House4 locals recommend
Cushing Memorial Park8 locals recommend

Other great vacation rentals in Ashland

Guest favourite
Home in Hopkinton
Hopkinton Mass 3+ Bedrooms - Great location!
Mar. 26 – Apr. 2
$222 CAD per night
4.95 out of 5 average rating, 137 reviews
Guest favourite
Guest suite in Uxbridge
Beautiful, Unique, & Cozy Cedar Flat
Oct. 14 – 21
$215 CAD per night
5.0 out of 5 average rating, 266 reviews
Superhost
Guest suite in Worcester
Enjoy your own private and cozy space!
Jul. 1 – 8
$123 CAD per night
4.83 out of 5 average rating, 339 reviews
Guest favourite
Apartment in Hudson
Newly Renovated Apartment Near Downtown Hudson
Apr. 27 – May 4
$217 CAD per night
4.93 out of 5 average rating, 416 reviews
Guest favourite
Cottage in Stow
White Pine Cottage
Jan. 18 – 25
$355 CAD per night
4.97 out of 5 average rating, 101 reviews
Superhost
Apartment in Framingham
Comfy Cute and lovely 1 BR APT w/Private Access.
May 21 – 28
$145 CAD per night
4.79 out of 5 average rating, 47 reviews
Guest favourite
Apartment in Framingham
Newly Renovated AP & parking
Apr. 3 – 10
$204 CAD per night
4.93 out of 5 average rating, 27 reviews
Guest favourite
Farm stay in Hopkinton
1790 Stone Manor Farm
Apr. 17 – 24
$592 CAD per night
4.97 out of 5 average rating, 94 reviews
Guest favourite
Home in Framingham
Cozy 3 Bedroom Renovated House
Jun. 1 – 8
$284 CAD per night
5.0 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Southborough
Willow Creek Cottage
Feb. 21 – 28
$211 CAD per night
4.96 out of 5 average rating, 25 reviews
Guest favourite
Loft in Medway
LA BOTTEGA
Aug. 29 – Sep. 5
$229 CAD per night
4.94 out of 5 average rating, 94 reviews
Guest favourite
Home in Holliston
All New Private Country Setting (2 Level-No Share)
May 29 – Jun. 5
$296 CAD per night
4.91 out of 5 average rating, 23 reviews

Destinations to explore