A river winding through a forest with autumn foliage.

Ashland Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Ashland holiday rentals

A living room with a sofa, a coffee table, a TV, and a hallway leading to other rooms.

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 AU$225
includes taxes & fees
21 Oct - 22 Oct
Private Luxury 2 Bedroom Suite
An outdoor patio with round tables and chairs, surrounded by green umbrellas.

2. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,324 reviews)
"Property was clean and cozy, convenient to the university and all the restaurants downtown!"
United States
kari
The price is AU$214
includes taxes & fees
4 Nov - 5 Nov
Crescent Suites Hotel
A modern hotel lobby with a seating area, a bar, and a kitchen.

3. Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very good, (259 reviews)
"Wonderful!!"
United States
Huynh
The price is AU$168
includes taxes & fees
1 Nov - 2 Nov
Residences at Solomon Pond
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

4. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"The house was nice. The beds were very comfortable. The house was close to everything. Check-in and check-out process was easy."
United States
Christina S.
The price is AU$764
includes taxes & fees
25 Oct - 26 Oct
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

5. 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, (33 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is AU$544
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A spacious living room with wooden beams, a sliding glass door to a patio, and a cozy seating area with a sofa and chairs.

6. Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
Framingham
10.0 out of 10, Exceptional, (3 reviews)
"Clean, pet friendly"
United States
Rebecca M.
Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
A living room with a grey sofa, two armchairs, a coffee table, and a large painting on the wall.

7. 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, (10 reviews)
"Very quiet, quaint and so cozy. We’re very satisfied with this property "
United States
roger n.
The price is AU$346
includes taxes & fees
3 Nov - 4 Nov
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

8. totally remodeled house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.2 out of 10, Wonderful, (17 reviews)
"Nicely located in neighbor with easy access to highways and walking distance to coffee shop this single home is perfect for being near Boston. Space is comfortable with all the comforts of home. "
United States
Karyn V.
The price is AU$494
includes taxes & fees
8 Nov - 9 Nov
totally remodeled house with fitness room, close to Boston and Worcester
A dining area with a round table, yellow chairs, a potted plant, and a Buddha painting on the wall.

9. 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
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
The price is AU$309
includes taxes & fees
21 Oct - 22 Oct
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

10. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (332 reviews)
"Clean hotel. The space was very nice and open, Very accessible to everything I needed"
United States
Krista
The price is AU$425
includes taxes & fees
11 Nov - 12 Nov
Kasa Boston at Fenway
A modern living room with a blue wall, a large window, a sofa, a coffee table, and a TV.

11. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (40 reviews)
"Location was very loud but thank God for earplugs. It was very clean but very old. Very expensive for such a location and room. I always believe in paying for what u get but I paid a lot for 3 nights."
United States
Luda
The price is AU$374
includes taxes & fees
9 Nov - 10 Nov
The Chester Hotel
A modern bathroom with a toilet, sink, and glass-enclosed shower.

12. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (342 reviews)
"The area was walkable and the room was great!"
United States
Edna
The price is AU$291
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 89 Marion
A compact hotel kitchen with a built-in microwave, a sink, and dark wooden cabinets.

13. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (454 reviews)
"Really pretty well maintained accomodation close to a lot of cool things to do in boston. its also pretty close to the train and bus station which was helpful to get around"
United States
Rakshitha
The price is AU$361
includes taxes & fees
1 Nov - 2 Nov
Maverick Suites at 28 Fenway
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

14. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (34 reviews)
"Great location, great Apartment"
United States
Carla Patricia
The price is AU$476
includes taxes & fees
3 Nov - 4 Nov
The Concord Hotel
A modern hotel room with a bed, a desk, a sofa, and a dining area.

15. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (243 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is AU$543
includes taxes & fees
9 Nov - 10 Nov
Charlesgate Suites
A row of brick buildings with storefronts, including a bakery and a liquor store.

16. Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (207 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is AU$345
includes taxes & fees
15 Nov - 16 Nov
Maverick Suites at 245 Newbury St
A spacious room with large windows, a wooden dining table with chairs, and a view of the outdoors.

17. 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 AU$370
includes taxes & fees
2 Nov - 3 Nov
Zen Inspired Retreat with Private Forest Trails
A white table with a vase of white orchids, a white chair, and a view of a cityscape through a window with a black frame.

18. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (183 reviews)
"Very well located. Close to two subways and Copeland Square."
Canada
Lorne
The price is AU$300
includes taxes & fees
9 Nov - 10 Nov
Maverick Suites at 400 Columbus Ave
Room

19. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (28 reviews)
"Great location. Exactly as pictured."
United States
Erica
The price is AU$574
includes taxes & fees
10 Nov - 11 Nov
Symple Live
A modern kitchen with white cabinetry, stainless steel appliances, a large island with bar stools, pendant lighting, and a view of the outdoors through a window.

20. 🎖The Ashmont Suite - Close to Subway + Downtown🎖

🎖The Ashmont Suite - Close to Subway + Downtown🎖
Dorchester
10.0 out of 10, Exceptional, (62 reviews)
"Is a great place"
United States
Ramon G.
The price is AU$787
includes taxes & fees
4 Nov - 5 Nov
🎖The Ashmont Suite - Close to Subway + Downtown🎖
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

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"first time staying and it was nice!"
Andrea 1-night trip
Posted 2 hours ago
The Midtown Hotel MOD Collection by Sonesta

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, 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 favourite 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 depend 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 AU$168 per night. Entering your travel dates in the search wizard might find you 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.