Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Ashland vacation rentals

Exterior

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, (156 reviews)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St
42-inch TV with satellite channels

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.2 out of 10, Good, (135 reviews)
"everything was great! only thing i’ll say is that the dots have some cracks where people can see in on the bathrooms and some rooms, but other than that i’d start here again!"
United States
Maelynn
Maverick Suites at 400 Columbus Ave
Interior entrance

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
8.2 out of 10, Very Good, (271 reviews)
"Great location for getting off and on the train and clean. We were on the first floor and it was very loud. You would hear people up and down the stairs. And if you have people staying in the room above you, you can hear everything. "
United States
samantha
The price is ￥14,614
￥30,550 total
includes taxes & fees
Jan 19 - Jan 20
Maverick Suites at 89 Marion
Terrace/patio

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,149 reviews)
"Everything about this facility was pleasing: clean, well-appointed, great kitchen, comfortable, well-located in the area. We were given a warm welcome when we arrived, provided with lots of information about Waltham. Located near shops and restaurants and on a walking trail along the Charles River. Highly recommend and would stay here again. "
Canada
Susan
Crescent Suites Hotel
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (335 reviews)
"Good place"
United States
Elijah
The price is ￥14,973
￥32,693 total
includes taxes & fees
Jan 21 - Jan 22
Maverick Suites at 28 Fenway
WiFi, bed sheets

The Chester: Vintage Elegance, Modern Comfort

The Chester: Vintage Elegance, Modern Comfort
2.0 star property
South End
The price is ￥18,539
￥47,813 total
includes taxes & fees
Jan 16 - Jan 17
The Chester: Vintage Elegance, Modern Comfort
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201 reviews)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
The price is ￥24,084
￥55,006 total
includes taxes & fees
Jan 18 - Jan 19
Charlesgate Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28 reviews)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
The price is ￥18,539
￥49,541 total
includes taxes & fees
Jan 21 - Jan 22
The Chester Hotel
TV

Cozy Fenway 1Br/1Ba | Close to Fenway Park!

Cozy Fenway 1Br/1Ba | Close to Fenway Park!
2.0 star property
Fenway–Kenmore
The price is ￥19,719
￥48,348 total
includes taxes & fees
Jan 16 - Jan 17
Cozy Fenway 1Br/1Ba | Close to Fenway Park!
Exterior

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68 reviews)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave
Interior

Residences at Solomon Pond

Residences at Solomon Pond
3.5 star property
Marlborough
8.2 out of 10, Very Good, (227 reviews)
"Plenty of drawers, cabinets in room. Modern appliances fostered a pleasant place. "
United States
Anonymous traveler
Residences at Solomon Pond
Fridge, microwave, oven, stovetop

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways

Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
2.0 star property
Lincoln
10.0 out of 10, Exceptional, (22 reviews)
"This is our second stay. We will definitely book again. Cleanliness is our priority. Location is great close to everything. The host makes sure everything you need is all here "
United States
Patty a.
The price is ￥15,687
￥30,527 total
includes taxes & fees
Jan 16 - Jan 17
Charming single family Cottage, pet friendly, close to Prov, Woon, MA & highways
Interior

Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!
Hyde Park
9.6 out of 10, Exceptional, (25 reviews)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
United States
TIARA V.
The price is ￥20,535
￥61,672 total
includes taxes & fees
Jan 16 - Jan 17
Hidden Gem right in the city of Boston!
Flat-screen TV

NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!

NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!
Roxbury
10.0 out of 10, Exceptional, (5 reviews)
"This is a lovely place to stay with you and your friends"
United States
Emily H.
The price is ￥50,950
￥144,486 total
includes taxes & fees
Jan 16 - Jan 17
NEW! Boston Full Home Near MBTA! 3 Mi To Fenway!
Exterior

Spacious Private Entrance Master Bedroom/Bath

Spacious Private Entrance Master Bedroom/Bath
Wellesley
10.0 out of 10, Exceptional, (90 reviews)
"Great place to stay. "
United States
Alexa
The price is ￥13,785
￥24,682 total
includes taxes & fees
Jan 28 - Jan 29
Spacious Private Entrance Master Bedroom/Bath
TV, offices

The Chester: Penthouse One Bedroom

The Chester: Penthouse One Bedroom
2.0 star property
South End
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely loved my stay. Great location, beautiful place. Clean and bright. We will be back!"
United States
Linda C.
The price is ￥36,760
￥72,400 total
includes taxes & fees
Jan 19 - Jan 20
The Chester: Penthouse One Bedroom
2 bedrooms, iron/ironing board, WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi

Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
Dedham
9.0 out of 10, Wonderful, (9 reviews)
"Very easy and accommodating stay right outside of the city. Would recommend for a stay. "
United States
Nolan B.
The price is ￥20,321
￥38,630 total
includes taxes & fees
Jan 16 - Jan 17
Cozy 2-bedroom apartment in charming Dedham - Legacy Mall with WiFi
TV, fireplace

2-bedroom in-law suite in soothing Framingham with AC comfort

2-bedroom in-law suite in soothing Framingham with AC comfort
2.0 star property
Framingham
The price is ￥8,873
￥13,451 total
includes taxes & fees
Jan 19 - Jan 20
2-bedroom in-law suite in soothing Framingham with AC comfort
TV, offices

The Chester: Modern Luxury, Historic Charm

The Chester: Modern Luxury, Historic Charm
2.0 star property
South End
9.0 out of 10, Wonderful, (2 reviews)
"Easy check in. Clean space. Cute decor and comfortable. Husband and I enjoyed the location. "
United States
Morgan Z.
The price is ￥28,679
￥61,836 total
includes taxes & fees
Jan 19 - Jan 20
The Chester: Modern Luxury, Historic Charm
Exterior

The Chester: Modern, Cool, Heart Of South End

The Chester: Modern, Cool, Heart Of South End
2.0 star property
South End
8.0 out of 10, Very Good, (1 review)
"The great thing about this is that the place looks EXACTLY like the photos. Very pleased about that. Some suggestions: could use some standing lamps or table lamps. The overheads doesnt make for a cozy ambience. It was either too bright or too dark, with them off. I think this would be an amazing place with better lighting. One glitch I experienced was that there was no remote control to the living room TV. Took about 3 days to get one, which was more than half my stay. Would have liked...
United States
Dorothy C.
The price is ￥23,768
￥55,282 total
includes taxes & fees
Jan 19 - Jan 20
The Chester: Modern, Cool, Heart Of South End
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

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Staff were extremely courteous, helpful, and friendly. Room was spotless."
HEIDI 1-night trip
Posted 22 hours ago
Hyatt Regency Boston/Cambridge

Find out more about Ashland

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Look no further and take a look at our great range of rental properties in Ashland!

Frequently asked questions

Are there vacation rentals in Ashland?

Yes, you can find vacation rentals near top local attractions in Ashland, or you can go with a more secluded option if you're looking for relaxation. 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 vacation rentals that Ashland has to offer?

Hidden Gem right in the city of Boston!: Visitors like this Ashland vacation home rental. It is located near skiing and offers a selection of games, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Fun and Games Family Entertainment Center, or get outside and enjoy nature at Cochituate State Park. Other places in town to visit include Hopkinton State Park and Ashland State Park.

What are vacation rentals like in Ashland?

Vacation rentals are private properties you can reserve for a couple days or more in Ashland. Vacation rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.