As local travel experts, we know what travelers are looking for when it comes to finding the perfect accommodations for their next trip. To compile our lists, we scour the internet to find properties with excellent ratings and reviews, desirable amenities, nearby attractions, and that something special that makes a destination worthy of traveling for.

We all deserve a break, even on a monthly basis. We work hard and want to leave the stresses of life behind sometimes, so why not take a quick getaway? In a state like Massachusetts, we don’t have to travel all that far to have a restful and relaxing staycation. If you are searching for ideas for getaways in Massachusetts, take a look at these magnificent escapes, one for each month of the year.

1. January: Home in Great Barrington

VRBO
Great Barrington, MA, USA
VRBO
Whether you enjoy the outdoor recreation like skiing and snowboarding offered at Butternut Ski Area & Tubing Center or just need some time in the Berkshires, this modernized home will make you want for nothing. With 1,000 square feet, three bedrooms, and one bathroom, a party of six can sleep comfortably here. Not only is it close to Butternut but it's just moments away from downtown Great Barrington and East Mountain Hiking Trails! Visit VRBO to learn more about this lovely getaway in Massachusetts.

2. February: Art House, Spacious Getaway in North Adams

VRBO
North Adams, MA 01247, USA
VRBO
If you enjoy art, you will love staying at the Art House. Located close to Mass MoCA, you can have an art-filled weekend this coming February. This Berkshires getaway has six bedrooms and two full baths and is fully remodeled. And if you time your stay right, you can be in town for the annual Winterfest.

3. March: Close to Mount Wachusett, Westminster

VRBO
VRBO
With its close proximity to Mount Wachusett, you may be able to catch the end of ski season in March at this lakeside home. If you're not into skiing, there are plenty of hiking trails around. This gorgeous accommodation in Massachusetts has two bedrooms and can sleep up to four people. There are also three bathrooms, a full kitchen, a living room area, and wonderful water views.

4. April: Vibrant Sterling Lakefront Lodge With Sailboat, Sterling

VRBO
Sterling, MA 01564, USA
VRBO
The warmer weather has arrived! Located in Sterling about ten miles from New England Botanic Garden at Tower Hill, this waterfront property will give you all the rest and relaxation you need. With three bedrooms and three bathrooms, up to see guests are easily accommodated. You can check out this Massachusetts getaway on VRBO.

5. May: Pebble House, a Waterfront Modern Home in Scituate

VRBO
Scituate, MA, USA
VRBO
Life is better on the water, right? In the month of May, it's still a little cool outside but if you're vacationing waterfront, we're sure you won't mind! This gorgeous, modern getaway spot in Massachusetts, has three bedrooms and five beds and can accommodate up to seven people. Not only do you have waterfront views, but you can walk to the harbor shops, restaurants, and the Scituate Lighthouse.

6. June: Artist's Studio turned Guest House, Rockport

VRBO
Rockport, MA, USA
VRBO
Only 450 square feet, this tiny house was once an artist's studio. Transformed into a charming guest house, this Massachusetts accommodation can sleep up to three guests. Enjoy views of the ocean from the deck or spend time in the cozy indoors. It's a great place to escape to!

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7. July: Private Unique Home, Walk to the Beach and Bay, Hull

VRBO
Hull, MA, USA
VRBO
The first floor of this unique Bay State getaway has an open-concept living room and kitchen space. Upstairs is where you'll find the bedroom. Spend some time outdoors by either walking to the beach and bay or heading out back to your very own private backyard featuring a grill and a seating area.

8. August: Private Cape Cod Cottage, Brewster

VRBO
Brewster, MA, USA
VRBO
It's not summer in Massachusetts without a trip to the Cape! This lovely Cape Cod rental is located in Brewster close to Ellis Landing Beach and Ocean Edge Resort. Not only is the location fabulous but this cottage is newly remodeled and can sleep up to five guests.

9. September: Beautiful Waterfront Cottage, Wellfleet

VRBO
Wellfleet, MA, USA
VRBO
Who says Cape Cod is just for summertime fun? Starting in September, visitors can enjoy the off-season with fewer tourists and crowds. This Massachusetts escape is located in Wellfleet and offers waterfront views of Drummer Cove. You'll experience all the quiet and privacy you could hope for here.

10. October: Private Rustic Cottage with Lake Access, New Marlborough

VRBO
New Marlborough, MA, USA
VRBO
There's no better place to be in the fall than in the Berkshires. Surround yourself with colorful fall foliage while enjoying Lake Buel. This cottage in Massachusetts has two bedrooms for up to six guests, a dining area, a lawn, a garden, and a shared dock if you would like to bring a boat. What a lovely place to relax in the fall!

11. November: Oceanfront with Peek-a-boo views of Cape Cod Bay, Plymouth

VRBO
Plymouth, MA, USA
VRBO
Spend some time in November in the town where the first Thanksgiving was held. This waterfront rental in Massachusetts has views of Cape Cod Bay and can sleep up to five guests. While you're staying in town, be sure to check out Plimoth Pawtuxet Museums to learn about the life of the Pilgrims and how they settled here.

12. December: Charming Unique Cottage with Mountain Views, West Stockbridge

VRBO
West Stockbridge, MA, USA
VRBO
Celebrate the holiday season or have easy access to the Berkshires for all your outdoor recreation needs with a stay in West Stockbridge. Located on top of a mountain, you'll enjoy spectacular views and scenery all around you. Spend time enjoying this cozy cottage before heading out into town.

Wouldn’t you just love to take one of these getaways in Massachusetts? Tell us what you think are some of the best places to stay in Massachusetts! Be sure to leave your thoughts in the comments section – we would love to hear from you.

If you prefer a day trip, check out this list of day trips in Massachusetts, one for each day of the year.

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

More to Explore

Vacation Destinations In Massachusetts

Katie Feldkamp | January 24, 2024

Where are some of the best vacation destinations in Massachusetts?

Massachusetts has it all. Charming towns, natural beauty both inland and along the coast, and plenty of history mixed with contemporary. Below is only a partial list of some of the most jawdropping places in Massachusetts, all of which you can visit and make your own vacation destination.

  • Castle Hill at The Crane Estate
  • The Cape Cod National Seashore
  • Bish Bash Falls in Mt. Washington
  • Martha’s Vineyard
  • Gay Head Cliffs, also on Martha’s Vineyard
  • Heritage Museums and Gardens in Sandwich

Check out the entire article to find out more about these and several more stunning places throughout Massachusetts.

What are some islands that have the best places to stay in Massachusetts?

There’s nothing like an island getaway, and the islands off the coast of Massachusetts are no exception. The next time you’re looking for an island getaway, consider these island getaways in Massachusetts:

  • Plum Island in Essex County
  • Castle Island in South Boston
  • Grape Island in the Boston Harbor Islands
  • Monomoy Island in Chatham
  • Crowninshield Island in Marblehead

Be sure to keep reading this full article for more information on these and several additional island destinations in Massachusetts.

What are some lakeside getaways in Massachusetts?

You don’t have to head to the coast to enjoy the waters of the Bay State. There are also incredible lakes worth a visit throughout Massachusetts. Some of the best lakes in Massachusetts include:

  • Laurel Lake in Erving
  • Long Pond in Harwich
  • Lake Quinsigamond in Worcester
  • Great Herring Pond in Cedarville and Plymouth
  • Lake Ashmere in Peru and Hinsdale

For more information in these and several other locations, check out this article on the best lakes in Massachusetts.

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