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

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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

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

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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

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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

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

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

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

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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

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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?

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

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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

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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

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

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

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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

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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

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

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.