Deals on vacations and trips to Ashland

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Ashland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Rockport House

The Rockport House

2 out of 5
Save 100% on your flight
Price was $1,085, price is now $769 per person
$769
per person
Jul 10 - Jul 13
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
This hotel features free WiFi in public areas, a garden, and laundry facilities. A virtual front desk are provided for your convenience.
Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Save 100% on your flight
Price was $2,301, price is now $1,287 per person
$1,287
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
A coffee shop, free WiFi in public areas, and a snack bar/deli are available at this hostel. Express check-in is also provided.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $1,863, price is now $1,140 per person
$1,140
per person
Jul 9 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $3,775, price is now $2,556 per person
$2,556
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
A private beach and a hot tub are featured at this guesthouse. Enjoy a day at the beach kayaking, or relax with sun loungers. WiFi in public areas is free.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,040, price is now $1,431 per person
$1,431
per person
Aug 24 - Aug 28
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

Top Ashland hotels deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
$185 nightly
The price is $215 total per night
$215 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Pet friendly
Free WiFi
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Free Cancellation
Reserve now, pay when you stay
$225 nightly
The price is $262 total per night
$262 total
Jun 7 - Jun 8
Total with taxes and fees
A gym is featured at this hotel, along with self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. There's a fireplace in the lobby and multilingual staff can provide around-the-clock assistance.
Breakfast included
Pet friendly
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street Boston MA
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $208 total per night
$208 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel

4 out of 5
39 Dalton St Boston MA
Free Cancellation
Reserve now, pay when you stay
$239 nightly
The price is $278 total per night
$278 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Pet friendly
DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
400 Soldiers Field Road Boston MA
Free Cancellation
Reserve now, pay when you stay
$163 nightly
The price is $190 total per night
$190 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like a free area shuttle.
Pool
Hot Tub
Boston Marriott Copley Place

Boston Marriott Copley Place

4 out of 5
110 Huntington Ave Boston MA
Free Cancellation
Reserve now, pay when you stay
$290 nightly
The price is $338 total per night
$338 total
Jun 7 - Jun 8
Total with taxes and fees
This traditional hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Pool
Free WiFi
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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.

Popular places to visit

Ashland State Park

3.5/5(2 reviews)

You can take time to visit Ashland State Park during your travels to Ashland. While you're in the area, wander around the parks.

Ashland State Park

Frequently asked questions

How much are vacation packages to Ashland?
Your travel fantasies can all come true in Ashland for as low as $769. Our affordable package deals include flights and hotels, so you'll find booking is nice and easy. All you'll have to focus on is having a good time.
How long should my Ashland vacation be?
Most travelers spend roughly 2 nights in Ashland, but how long you stay is totally up to you. If you're hoping to explore all the exciting things this destination has to offer, why not hang around for a couple of extra nights?
Where can I get the best vacation package deals for Ashland?
It's hard to top Travelocity when it comes to piecing together your Ashland package deal. There are at least 400 air carriers and 1,000,000 properties around the world to choose from. Plan your escape now and get ready to cross another destination off your must-see list.
Why should I purchase my Ashland vacation package with Travelocity?
Because life is one big journey, and we offer all you need to get you on your way. With our high-quality service and Price Match Guarantee, you can book with confidence. What's more, you can rest easy while you're on the road knowing we're always available to chat via our 24/7 customer support.
Can I save money on my Ashland car rental if I bundle it with hotels and flights?
You certainly can — bundle your hotel, flight and car into an Ashland vacation package and you'll save a tidy sum. With so much to see and do in and around Ashland, having your own ride will make exploring easy. Once you've settled into the driver's seat, turn up the stereo and head to Plymouth Rock, an unmissable attraction approximately 45 mi from Ashland.
Which airport is best for Ashland?
Logan Intl. Airport (BOS) is one of the most popular airports in Ashland. It's around 25 mi east of the bustling downtown area. Your other options are T.F. Green Airport (PVD) (35 mi away from central Ashland) and Manchester-Boston Regional Airport (MHT) (45 mi away from central Ashland).
What is there to do in Ashland?
Ashland State Park should be on your travel schedule. After you've crossed off this famous attraction, amble through the streets of Ashland and discover what makes this exciting place tick.
Where should I stay when visiting Ashland?
Many people check in to the Warren Conference Center and Inn. It's a terrific base for your Ashland getaway.

Photos of local treasures

Browse Ashland vacation photos for more inspiration

Ashland Reservoir aerial view with fall foliage in Ashland State Park in town of Ashland, Massachusetts MA, USA.
Ashland town center aerial view including Federated Church and Town Hall in Ashland, Massachusetts, USA.
Ashland town center aerial view including Federated Church and Town Hall in Ashland, Massachusetts, USA.
Ashland