You've packed your bags, and booked your flight (or Uber), and now all that's left is to find the perfect Massachusetts spot to spend your precious vacation days. If you're looking to venture outside the ordinary and have an incredible experience, take a look at these jaw-dropping and unique places to stay in Massachusetts.
Treehouse Rentals in Massachusetts
Treehouses aren't just for kids you know. Us adults can stay up in the treetops as well. Check out these extraordinary treehouse rentals in Massachusetts that will make you (almost) feel like a kid again, but with many more amenities.
1. Modern Treehouse in Truro Hills, Truro
- Address: Truro, MA
- Size: 3 bedrooms, 3 bathrooms
- Price: $461/night
- Amenities: Wireless internet, washer/dryer, full kitchen, grill, water sports gear
- Ratings: 4.9 stars
This treehouse is one of the most unique rentals in Massachusetts. Its setting among the trees gives the ultimate privacy, especially in a town as rural as Truro. However, you will enjoy plenty of modern amenities while you're here and you'll be in close proximity to the Cape Cod National Seashore, Provincetown, and Wellfleet. Book your stay on Vrbo.
2. Serene Berkshires Cabin With Deck & Fire Pit, Otis
- Address: Otis, MA
- Size: 4 bedrooms, 3 bathrooms
- Price: $319/night
- Amenities: Fire pit, washer/dryer, cable television, grill
While not technically a treehouse, the interior of this home is certainly reminiscent of one. Throughout the home, you'll see wood paneling, and the climb up to the second story where the bedrooms are will definitely give you the feeling of a treehouse. You'll also be able to spend time out on the deck overlooking the forest. Book your stay on Vrbo.
Tiny Home Rentals in Massachusetts
Tiny homes are a bit of a novelty these days. But there are plenty of reasons why they are so popular. Discover why for yourself by spending time in one of these tiny home rentals in Massachusetts.
3. Sand Pebble Cottage, Dennis Port
- Address: Dennis Port, MA
- Size: 1 bedroom, 2 bathrooms
- Price: $141/night
- Amenities: Pet-friendly, air conditioning, washer/dryer, outdoor furniture, 2 bicycles, Smart TV
- Ratings: 4.8 stars
Welcome to Sand Pebble Cottage, a tiny home rental that's close to beaches as well as the village of Dennis Port. There are two adult bikes provided so biking to the beach or into town is always an option. And you will enjoy a lovely stay here when you're not out exploring. Book your stay on VRBO.
4. Perfect Couples Getaway by the Sea, Nantucket
- Address: Nantucket, MA
- Size: Studio, 2 bathrooms
- Price: $334/night
- Amenities: Wireless internet, kitchen, grill, beach chairs
- Ratings: 4.9 stars
Sail away to the island of Nantucket for a relaxing getaway at The Tiny House. Located in Siasconset, coming here is a step back in time and you'll experience plenty of peace and quiet. And, while small, this home certainly doesn't lack character or water views for that matter. Book your stay on VRBO.
Farm Houses for Rent in Massachusetts
Is farm life for you? Well, you can certainly find out or at least pretend you're living on a farm by spending some time at a farmhouse rental in Massachusetts. These rural getaways are set away from city life and may give you the relaxation you deserve.
5. High Pocket Vacation Rental, Colrain
- Address: Colrain, MA
- Size: 3 bedrooms
- Price: $350/night
- Amenities: Air conditioning, heating, hot tub, full kitchen, grill, kayak/canoe, bicycles, snowshoes, fire pit
- Ratings: 4.9 stars
Experience life in the country at this farmhouse in Colrain. Set on 545 idyllic acres, this home can be rented any time of year. During the winter, guests can go snowshoeing. In the warmer months, kayaking, canoeing, boating, and biking are all great options for outdoor recreation in the area. You'll also be close to skiing and golfing at a nearby golf course. The house itself is over 220 years old and uses solar power. There's also a game room and a hot tub, so if you're looking for fun places to stay in Massachusetts, this should be a strong contender! Book your stay on VRBO.
6. Historic Farmhouse, Williamsburg
- Address: Williamsburg, MA
- Size: 3 bedroom, 1 bathroom
- Price: $236/night
- Amenities: Wi-Fi, full kitchen, outdoor furniture, fire pit, Smart TV, books, games
- Ratings: 5 stars
Enjoy the tranquility that often comes with farm life by staying at this farmhouse in Williamsburg. You can even visit with the goats and ducks that call this farm home and stroll through the fields and gardens. You'll feel so at peace here! Book your stay on VRBO.
Mansions for Rent in Massachusetts
If tiny houses aren't for you, how about the exact opposite? With an air of opulence, you can live the high life for a while by renting a mansion in Massachusetts.
7. Villa Fiori, Manchester-by-the-Sea
- Address: Manchester-by-the-Sea, MA
- Size: 10 bedrooms, 6 bathrooms
- Price: $750/night
- Amenities: 7 fireplaces, washer/dryer, gourmet kitchen, grill
- Ratings: 4.7 stars
This opulent Italian villa on the New England coast will make you want for nothing. You'll enjoy feeling like royalty so much that you may never want to leave once you check in. This home is a spacious 6,500 square feet with 10 bedrooms, six bathrooms, and a gourmet kitchen with two ovens and two dishwashers. Feel free to spend the day relaxing in the sitting room, cooking up a meal, or walking to the nearby beach. This is luxury at its finest! Book your stay on VRBO.
8. The Playhouse, Lee
- Address: Lee, MA
- Size: 6 bedrooms, 5 bathrooms
- Price: $1,332/night
- Amenities: Washer/dryer, fitness room, 2 full kitchens, canoe, water sports gear, fire pit
- Ratings: 4.9 stars
If you're looking for cool places to stay in Massachusetts, look no further than The Playhouse. This aptly-named home is 7,000 square feet of unique decor, amenities, and fun. With the ability to accommodate up to 20 guests, maybe consider this large-scale home for your next reunion. Book your stay on VRBO.
9. Luxury 9 BR Home With Pool, Downtown Chatham
- Address: Chatham, MA
- Size: 9 bedrooms, 12 bathrooms
- Price: $1,675/night
- Amenities: Private outdoor heated pool, spa whirlpool, gourmet kitchen, fire pit, game room
- Ratings: 4.9 stars
Everything about this massive beach house on Cape Cod screams "luxury." Located in downtown Chatham, this 1877 historic house has been renovated into luxurious accommodations. While you can always hit the beach, you may prefer to lounge by your very own private pool instead. Spend some time cooking in the gourmet kitchen that comes complete with two refrigerators plus a wine fridge. This place is perfect for a large gathering especially if you prefer to be close to the beach. Book your stay on VRBO.
Castles for Rent in Massachusetts
As if mansions weren't big or luxurious enough, we have added a castle-like place to the mix of unique places to stay in Massachusetts. This gorgeous estate is over the top in terms of luxury and amenities and will make you believe you're staying in a castle.
10. The Kemble, Lenox
- Address: Lenox, MA
- Size: 13 bedrooms, 14 bathrooms
- Price: $3,333/night
- Amenities: Washer/dryer, fitness room, hot tub, sauna, kayak/canoe, boat, gaming room, 7 fireplaces
- Ratings: 4.9 stars
Originally built in the 1880s for a U.S. Secretary of State and New Jersey Senator, The Kemble is an immense 15,000-square-foot Great Estate. With its sheer size, complete with 13 guest rooms, you can certainly host a family or friends reunion. If you enjoy cooking, you'll love the gourmet kitchen and the use of herbs and vegetables from the garden. If you have kids with you, they will certainly enjoy the gaming room while adults may be partial to the library, the bar, or the music room. Book your stay on VRBO.
Which of these unique places to stay in Massachusetts will you book first? Sometimes the destination definitely trumps the journey. If you're looking to spend a few nights sleeping under the stars, here are some of the most beautiful campsites in Massachusetts to do just that.
Subscribe to our newsletter
Get the latest updates and news
Thank you for subscribing!