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 ours, we don’t have to travel all too 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.
- January: Home in Great Barrington
VRBO
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. Great Barrington, MA, USA
- February: Art House, Spacious Getaway in North Adams
VRBO
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. North Adams, MA 01247, USA
- 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
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. Sterling, MA 01564, USA
- May: Pebble House, a Waterfront Modern Home in Scituate
VRBO
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. Scituate, MA, USA
- June: Artist’s Studio turned Guest House, Rockport
VRBO
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! Rockport, MA, USA
- July: Private Unique Home, Walk to the Beach and Bay, Hull
VRBO
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. Hull, MA, USA
- August: Private Cape Cod Cottage, Brewster
VRBO
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. Brewster, MA, USA
- September: Beautiful Waterfront Cottage, Wellfleet
VRBO
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. Wellfleet, MA, USA
- October: Private Rustic Cottage with Lake Access, New Marlborough
VRBO
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! New Marlborough, MA, USA
- November: Oceanfront with Peek-a-boo views of Cape Cod Bay, Plymouth
VRBO
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. Plymouth, MA, USA
- December: Charming Unique Cottage with Mountain Views, West Stockbridge
VRBO
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. West Stockbridge, MA, USA
Wouldn’t you just love to take one of these getaways in Massachusetts? Tell us your favorite on the list! If you prefer a day trip, check out this list of day trips in Massachusetts, one for each day of the year.
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.
Great Barrington, MA, USA
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.
North Adams, MA 01247, USA
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.
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.
Sterling, MA 01564, USA
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.
Scituate, MA, USA
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!
Rockport, MA, USA
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.
Hull, MA, USA
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.
Brewster, MA, USA
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.
Wellfleet, MA, USA
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!
New Marlborough, MA, USA
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.
Plymouth, MA, USA
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.
West Stockbridge, MA, USA
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