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Our top choices for Ashland holiday rentals

1. Private Luxury 2 Bedroom Suite

Private Luxury 2 Bedroom Suite
Framingham
8.2 out of 10, Very good, (14 reviews)
"Overall we had a great time"
United States
David W.
The price is £116
includes taxes & fees
18 Nov - 19 Nov
Private Luxury 2 Bedroom Suite

2. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,358 reviews)
"Wehave stayed here several times and each time has been a pleasure."
United States
Kasandra
The price is £116
includes taxes & fees
15 Dec - 16 Dec
Crescent Suites Hotel

3. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (36 reviews)
"We had a great stay."
United States
Jessica D.
The price is £282
includes taxes & fees
30 Nov - 1 Dec
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

4. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (269 reviews)
"Friendly front desk. Clean and pleasant room. Would stay again."
United States
Tae
The price is £95
includes taxes & fees
23 Nov - 24 Nov
Residences at Solomon Pond

5. Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (11 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is £163
includes taxes & fees
1 Dec - 2 Dec
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

6. Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
The price is £171
includes taxes & fees
1 Dec - 2 Dec
Beautiful family getaway, walking distance to markets, 35 min drive to Boston

7. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (352 reviews)
"Great location, very comfortable apartment, great facilities, everyone was friendly and helpful!!!"
United States
antonio
The price is £224
includes taxes & fees
1 Dec - 2 Dec
Kasa Boston at Fenway

8. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (45 reviews)
"I had a great stay at The Chester Hotel. Super cute vibe, easy check-in, and good location for where I needed to be for work. Bed is super comfy, the room aesthetic is great and the restaurant MIDA next door was really good!"
United States
Tracy
The price is £203
includes taxes & fees
25 Nov - 26 Nov
The Chester Hotel

9. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (357 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is £134
includes taxes & fees
22 Nov - 23 Nov
Maverick Suites at 89 Marion

10. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.4 out of 10, Very good, (219 reviews)
"Great location - plenty to do."
United States
Chloe
The price is £146
includes taxes & fees
2 Dec - 3 Dec
Maverick Suites at 245 Newbury St

11. Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely place to stay! This site was meticulously clean, gardens and decor both zen and whimsical, trails well maintained, near a grocery and other shopping. I will stay again!"
United States
Melanie S.
The price is £187
includes taxes & fees
7 Dec - 8 Dec
Zen Inspired Retreat with Private Forest Trails

12. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (479 reviews)
"Great location and the room was nicely decorated and clean!"
United States
Judy
The price is £162
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 28 Fenway

13. Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026
Westwood
10.0 out of 10, Exceptional, (8 reviews)
"Easy-to-find location and charming accommodations. Everything was organized well and very clean. Would highly recommend this listing."
United States
Eva O.
The price is £235
includes taxes & fees
21 Nov - 22 Nov
Welcome in this charming one bedroom apartment located in Westwood. WorldCup2026

14. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.2 out of 10, Very good, (41 reviews)
"Super nice place to stay plus it was super close to shopping and all the sights"
Canada
Rupintal
The price is £212
includes taxes & fees
23 Nov - 24 Nov
The Concord Hotel

15. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (247 reviews)
"Spacers, convenient location"
United States
Svetlana
The price is £280
includes taxes & fees
23 Nov - 24 Nov
Charlesgate Suites

16. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (31 reviews)
"Great location. Exactly as pictured."
United States
Erica
The price is £229
includes taxes & fees
13 Dec - 14 Dec
Symple Live

17. Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very good, (101 reviews)
"Enjoyed the stay"
United States
Frances
The price is £131
includes taxes & fees
13 Dec - 14 Dec
Maverick Suites at 402 Columbus Ave

18. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
9.0 out of 10, Wonderful, (2 reviews)
"Nice and very clean. Host communicated fast and helpful."
United States
Ekaterina
The price is £82
includes taxes & fees
15 Nov - 16 Nov
Clean & Cozy Private-3 floor_R 2

19. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is £182
includes taxes & fees
18 Nov - 19 Nov
Large 3BD 1st Floor Apartment Minutes from 290

20. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is £256
includes taxes & fees
15 Nov - 16 Nov
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
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 Ashland Hotel Reviews

Find out more about Ashland

Everything you need to know about Ashland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ashland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland holiday rentals we have selected for you start as low as £95 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Ashland?

Yes, there are holiday rentals close to the most popular sights in Ashland, or you can select a more secluded option if you're looking for a relaxing stay. Ashland is known for its shopping and restaurants. Make sure you have time to check out the lake views while you're in the area.

What are some of the best holiday rentals that Ashland has to offer?

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking: This holiday home rental outside of Ashland has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Ashland?

Expedia has 3 holiday rentals for your stay in Ashland.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Jordan's Furniture, or get outside and enjoy nature at Cochituate State Park. Other places in town to visit include Ashland State Park and Hopkinton State Park.

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for families.