Here Are The 18 Absolute Best Places To Stay In Massachusetts
Michelle
Author
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.
Deciding where to stay in Massachusetts can get a bit overwhelming. With big cities and small towns, there are seemingly endless options for accommodations in Massachusetts. The Bay State might not be the largest in the country, but it certainly packs a punch when it comes to overnight stays. From mountain retreats to beachside getaways, we’ve found the best vacation rentals in Massachusetts suitable for a variety of budgets. Whether you’re looking for a vacation that won’t break the bank or a retreat that’s perfect for families, there’s something for everyone who wants to experience the beauty of New England. Let’s take a look at some of the best places to stay in Massachusetts.
Best Affordable Places to Stay in Massachusetts
Going on vacation doesn’t have to mean spending every last dollar on a place to sleep. If you’re looking for great accommodation in Massachusetts, but don’t want to break the bank these are some of the best options to explore.
1. Quiet Cul-de-sac Home, Provincetown
- Location: Provincetown, MA
- Size: 2 bedrooms (sleeps 4), 2.5 baths
- Price: $174/night
- Amenities: Wi-Fi, Full Kitchen, Washer & Dryer, Fireplace, Grill, Patio
- Rating: 4.7 stars
This delightful charmer in Provincetown is located in a quiet neighborhood only a half-mile walk from Commercial Street which runs through the heart of downtown. Enjoy cute shops, historic sites, cozy cafes, and darling restaurants overlooking the bay. Whether you are in town for a couple's getaway or a family vacation this cute home is ready to welcome you on your next adventure to The Cape.
2. Direct Ocean Front Home, Marshfield
- Location: Marshfield, MA
- Size: 3 bedrooms (sleeps 7), 2 full baths
- Price: $186/night
- Amenities: Direct Ocean Front Access, Water Sports Gear, Flat Screen TVs, Fire Pit
- Ratings: 5 stars
While the beach is a no-brainer in the summer, the off-season offers just as much beauty and more affordable pricing. Head to the small town of Marshfield, located on the South Shore, to soak up the coast without the long drive to Cape Cod. This home sits directly on the water for some of the best Atlantic views in the area. It was newly remodeled and no stones were left unturned. You’ll love the outdoor access, including close proximity to golf courses. But on a rainy day, this vacation rental is cozy as can be.
3. Rustic Tiny House, Leicester
- Location: Leicester, MA
- Size: 1 bedroom (sleeps 2), 1 bath
- Price: $96/night
- Amenities: Kitchenette, Dedicated workspace, Firepit, Grill, Kayak
- Rating: 4.97 stars
Here we have a Rustic Tiny House with water access. Located at Southwick Pond, feel free to kayak or go for a hike in the area. Perfect for those who enjoy the outdoors, this small abode is also affordable. Keep in mind, however, that it is rustic. There is no running water as well as a composting toilet. However, the grounds include a camp sink and an outdoor shower with hot water. The interior is quite comfortable and includes a memory foam bed and a small kitchen along with a living room area.
4. The Lake Cottage, Orange
- Location: Orange, MA
- Size: 1 bedroom (sleeps 2), 1 bath
- Price: $120/night
- Amenities: Kitchen, private dock, lake access
- Rating: 4.94 stars
What was once an ice fisherman's shack is now a gorgeous updated Lake Cottage. Perfect for two, you'll have access to a small lake complete with a private dock. Go fishing or swimming or just sit at the shore gazing out at the water. It's so serene! Indoors, you'll find a comfortable space complete with a bedroom and queen-sized bed, an open living room area, and a kitchen. There are also games and a record player free for you to use during your stay. This is one of the most charming vacation rentals in Massachusetts if you ask me!
Best Places to Stay in Massachusetts for Families
Traveling with family means creating memories that will last a lifetime. But, all those memories can be hard to make if you haven’t chosen a place that’s perfect for all ages. The options here are sure to appeal to everyone in your group, ensuring you spend as much time as possible laughing and enjoying your time together.
5. Sun-Dappled Retreat, Wickaboag Lake
- Location: West Brookfield, MA
- Size: 2 bedrooms (sleeps 7), 2.5 baths
- Price: $433/night
- Amenities: Spacious Backyard, Outdoor Dining Area, Media Room, Close Proximity to Nature
- Ratings: 5 stars
This beautiful home located in West Brookfield offers fantastic access to some of the best nature in Worcester County. And, it’s not far from the Berkshires or Lenox. With 3,000 feet of space to enjoy, this is an ideal choice for those looking to travel with friends and family. It sleeps seven so there’s no excuse not to bring everyone! The home has plenty of indoor space, but nature lovers will appreciate the huge deck and backyard. Best of all, this vacation rental in Massachusetts is within walking distance from Wickaboag Lake and less than two miles from West Brookfield State Forest. Even history buffs will have something to do as Old Sturbridge Village is just 14 miles from the house.
6. The Beach Glass Cottage, Hyannis
- Location: Hyannis, MA
- Size: 3 bedrooms (sleeps 7), 2 full baths
- Price: $350/night
- Amenities: Renovated Kitchen, Downtown Access, Waterfront Access, Fire Pit
- Ratings: 5 stars
Make it a family-friendly beach getaway with this beautiful home in Hyannis. The cottage sits directly on a small pond, making it perfect for small kids just getting used to the water. For a full Cape Cod beach day, visitors can make their way to either Craigville Beach or Keyes Memorial Beach which are each about 1.5 miles away. To enjoy a vacation from the vacation, the Beach Glass Cottage offers access to ferries that will take the whole family to Nantucket or Martha’s Vineyard.
7. Waterfront Lake House, Sturbridge
- Location: Sturbridge, MA
- Size: 3 bedrooms (sleeps 8), 2 full baths
- Price: $358/night
- Amenities: Lakefront Access, Water Sports Gear, Games, Fire Pit, Spacious Rooms
- Ratings: 5 stars
Located on a peninsula at the shores of the lake, there’s a view from every window in this beautiful cabin. It has plenty of room between its three bedrooms and common space, but there’s a good chance you’ll want to spend most of your time outside. Between boating, fishing, and swimming this getaway is perfect for a family who loves to enjoy time outside. Plan on staying for a week to enjoy everything the area has to offer including hiking and entertainment.
Best Romantic Places to Stay in Massachusetts for Couples
These Bay State getaways are perfect for quiet time alone, while also enjoying everything Massachusetts has to offer. Get away from it all with some of our favorite options here.
8. Maushop Village Cottage, New Seabury
- Location: New Seabury, MA
- Size: 2 bedrooms (sleeps 5), 1 full bath
- Price: $325/night
- Amenities: Fast Wi-Fi, Full Kitchen, Washer & Dryer, Grill, Beachfront
- Rating: 4.9 stars
This darling beach cottage in the desirable private Maushop Village beach community is ready for your romantic weekend in New England. Walk to the Popponesset Marketplace to enjoy the many local award-winning restaurants, public gardens, art galleries, and coffee shops. If you are wondering where to stay in Massachusetts to treat that someone special to a memorable getaway, this Maushop Village cottage is a delightful choice.
9. Eliza Cottage, Nantucket Town
- Location: Nantucket, MA
- Size: 1 bedroom (sleeps 4), 1 full bath
- Price: $1,100/night
- Amenities: Wi-Fi, Gourmet Kitchen, Sonos Music System, Washer & Dryer, Grill, Access to Nantucket Club (Swimming Pool, Hot Tub, Fitness Center, Sauna, Game Room)
- Rating: 5 stars
Eliza Cottage is one of the most coveted rentals in Nantucket as it neighbors the exclusive White Elephant Nantucket hotel. During your stay you'll enjoy views of the Brant Point Lighthouse as it stands sentry at the mouth of the harbor. You'll take a stroll to Main Street and enjoy all of its charm. Or, you could spend a quiet morning walking along Children's Beach. To round out the evening, the gentle ping of sailboat rigging dancing in the wind orchestrates a symphony as the sun sets on another eventful day. When you book Eliza Cottage you'll share these experiences and more with someone you hold dear. Can you think of a more romantic getaway?
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10. Annisquam Village Bunny Cottage, Gloucester
- Location: Gloucester, MA
- Size: 1 bedroom (sleeps 3), 1 full bath
- Price: $225/night
- Amenities: Wi-Fi, Bluetooth Sound System, Kitchenette, Beach Access
- Rating: 4.96 stars
This gorgeous cottage was renovated by a pair of artists so it's absolutely charming! Not only does the Annisquam Village Bunny Cottage have everything you need for a romantic getaway but it's close to Lighthouse and Cambridge Beaches as well as a restaurant. The grounds of this home have gardens and beach views from the bedroom window. It's hard not to fall in love with a place like this.
11. Glamorous Cabana, Newbury
- Location: Newbury, MA
- Size: 1 bedroom (sleeps 2), 1 full bath
- Price: $180/night
- Amenities: Wi-Fi, Shared Pool, Indoor Gas Fireplace, Dedicated Workspace
- Rating: 5 stars
The Glamorous Cabana in Newbury is the ultimate romantic getaway! Inside there's a cozy, comfortable queen bed, a bistro-style dining table, and a fireplace. French doors open up to the back patio where you'll have access to the shared pool and plenty of seating. You and your partner may never want to leave this unique Airbnb in Massachusetts!
Best Places to Stay in Cape Cod
If you’re willing to invest the time it can take to drive to The Cape you want to be certain the destination is worth it! With the two picks featured here, the stress of Route 3 will melt away. Our third featured rental is technically north of Cape Cod, but with the stunning views of Cape Cod Bay, it certainly deserves a mention.
12. Tidal Cove Home, Wellfleet
- Location: Wellfleet, MA
- Size: 3 bedrooms (sleeps 6), 3 full baths
- Price: $294/night
- Amenities: Water Views, Smart TV, Equipped Kitchen, Spacious Rooms
- Ratings: 4.8 stars
Located almost in the center of Cape Cod, Wellfleet has an entirely different feel than the rest of the region. And, this home located overlooking a tidal pool, mirrors that feel. The home is surrounded by pines and a perennial garden, offering plenty of privacy. That also means lots of peace and tranquility. This is the perfect spot if you’d like to be near the water, without the hustle and bustle of the beachfront communities. Be sure to carve out some time to enjoy the two-story wall of glass that provides sweeping views over the water. Or, hop in the car for a trip to Provincetown or Harwich. Of course, you can also use this home as a base for long drives with ocean views.
13. The Flying Fish, South Chatham
- Location: South Chatham, MA
- Size: 4 bedrooms (sleeps 11), 2.5 baths
- Price: $328/night
- Amenities: Ping Pong Table, Foosball, Hot Tub, Water Views, Free Parking
- Ratings: 4.9 stars
This is the perfect home for a group of friends or a family who are looking to spend time together near the water. With sleeping for 11, there are plenty of guest rooms with a lot of opportunities for fun to be had. The home features an open-concept kitchen which means nobody is left out of the fun. Enjoy time with the family at the foosball table and then grill on the deck. Of course, with the beach and downtown Chatham nearby there’s a good chance you’ll be out of the house the majority of your time here. With the free parking, no need to move the car. Make sure to visit Chatham Bars Inn, or hop in the car for a trip to Brewster, Falmouth, or Dennis.
14. Cliff House, Plymouth
- Location: Plymouth, MA
- Size: 4 bedrooms (sleeps 8), 4.5 baths
- Price: $1,140/night
- Amenities: 500+ Mbps internet, High-End Linens, Gourmet Kitchen, Washer & Dryer, Gas Fireplace, Grill, Hot Tub, Fire Pit, Oceanfront
- Rating: 5 stars
When you imagine a getaway to Cape Cod Bay this is the home you should be picturing in your mind. Breathtaking sunsets, stunning views of The Cape from the living room and bedrooms, and the opportunity to kayak with dolphins right from your private beach. The home itself was built with five-star amenities as if you were staying at a luxury resort. But the most important thing of all is the memories you'll make with your family that will last a lifetime.
15. Waterfront Lake Cottage, Sandwich
- Location: Sandwich, MA
- Size: 1 bedroom (sleeps 2), 1 bath
- Price: $231/night
- Amenities: Wi-Fi, Dedicated Workspace, Gourmet Kitchen, Washer & Dryer, Private Beach
- Rating: 4.95 stars
Once upon a time, this Waterfront Lake Cottage in Sandwich was a boat house. Once a rustic storage place for boats, it's a modernized home with gorgeous water views and a private beach with lake access the moment you step outside. As you probably know, Cape Cod is much more than the ocean and bay -- there are more than 200 kettle ponds on the peninsula, including this one. After staying here, you'll believe it's one of the best Airbnbs in Massachusetts.
Best Places to Stay in Boston
One of the country’s best cities is right here in Massachusetts and it offers tons to do. From smaller neighborhoods to downtown, Fenway Park to the Back Bay to Boston Common to the Seaport and Cambridge there’s always something happening in and around this city. For many in the state it’s easy to make a day trip, but consider spending a long weekend and you might be surprised at just how busy you are! Forget the Hilton, Marriott, and other luxury hotels, all you need are these wonderful vacation rentals.
16. Apartment with Roof Deck, Little Italy
- Location: Boston, MA
- Size: 1 bedroom (sleeps 2), 1 full bath
- Price: $358/night
- Amenities: Roof Deck, Access to Restaurants, Views
- Ratings: 5 stars
If there’s one thing we love about Boston it’s the culture and you’ll find it right outside your door with a stay at this Little Italy apartment. Centrally located in the North End, visitors will have views of Boston Harbor, the USS Constitution, and the USS Cassin Young. It’s also a short 10-minute walk to hot spots like the TD Garden, Freedom Trail, and public transportation. Dining options are everywhere (including plenty of Italian) and access to downtown Boston can’t be beaten. Everything you need seems to be on-site, giving it the real feel of a bed and breakfast.
17. Bright & Spacious Loft, Downtown Crossing
- Location: Boston, MA
- Size: 1 bedroom (sleeps 4), 1 full bath
- Price: $410/night
- Amenities: Wheelchair Accessible, Smart TV, Central A/C
- Ratings: 4.9 stars
Modern vibes are all over this beautiful loft located right near the Freedom Trail. The open-concept loft feels like a boutique hotel and is located right downtown which means access to the best of the city. Make your way to Faneuil Hall or spend some time shopping on Newbury Street. Take in a Red Sox game or simply stay at the loft and enjoy the free Wi-Fi. The space has a bedroom with a Queen-sized bed but also offers a pull-out couch on which to sleep. On sunny days guests will be drenched in the sun, which makes everything seem even roomier than it already is. Plan on a weekend away here for a special occasion, or for the next time you have tickets to a show in the city.
18. Designer 1-BR Apt, Historic Charlestown
- Location: Charlestown, MA
- Size: 1 bedroom (sleeps 2), 1 full bath
- Price: $237/night
- Amenities: Wi-Fi, Washer & Dryer, Board Games, Central Heating, A/C
- Ratings: 5 stars
This Designer 1-Bedroom Apartment is a bright and airy space that has all you need to enjoy your stay in Boston. Its premier location is in the historic Charlestown neighborhood. You can walk to shops, restaurants, and more from this apartment. It's also by an MBTA station for easy access around the city. Enjoy your stay!
Have you spent the night at any of these beautiful accommodations in Massachusetts? Are there any other rentals you’d add to our best places to stay in Massachusetts list? Let us know in the comments!
And, for those looking for a bit more privacy consider renting this entire island in Massachusetts.
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More to Explore
Where To Stay in Massachusetts
What are the best unique hotels in Massachusetts?
The most unique hotels in Massachusetts offer fun stays throughout the state. They might be harder to find, but there are plenty that offer getaways that are far different than your typical luxury hotel. Some of the most unique hotels in Massachusetts are:
- The Green Turtle, Boston
- The Deerfield Inn, Deerfield
- HI Boston, Chinatown in Boston (this one offers bunkbeds!)
- Liberty Hotel (a former jail!), Beacon Hill in Boston
There are plenty of ways to spend a night in Massachusetts that don't include a chain hotel. Choose any of these for an unforgettable experience!
Where are the most unique getaways in Massachusetts?
The most unique getaways in Massachusetts can be found in every corner of the state. From the Berkshires to Cape Cod, there's something for everyone. For those who prefer water, The Cape is a natural choice. Consider a long weekend in Wellfleet to take in a part of Cape Cod that isn't as crowded. Those who love chilly weather will enjoy a weekend picking apples near a fantastic cabin. A fun getaway at Jaeschke's Orchard on Gould Road in Adams offers a cozy time for a couple. History buffs will appreciate a visit to Northhampton and a stay at the Brookside Carriage House dating back to the 1890s. One of America's best hidden gem towns, Salisbury, is near Boston and also offers a fun way to escape for a weekend.