
Vacation rentals in Massachusetts
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Top-rated vacation rentals in Massachusetts
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Cider House Cottage
Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Lionsgate at Cohasset
Lionsgate is the perfect retreat to refresh the soul. Newly remodeled fully stocked kitchen with comfortable amenities provide a home away from feel. Enjoy a roaring fire in a rustic cabin during the winter or the coolness of a mini split in the summer. Cohasset, jewel of the South Shore is a quintessential New England seaside village located half way between Boston and Cape Cod. The ocean offers abundant recreation opportunities as well as plentiful parks for hiking and biking. A must visit.

Gingerbread House Tower in the Berkshire Hills
Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Peaceful Lake Views from Private Hot Tub
Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for a week long getaway with 2 work spaces. 25 minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Entire Historic Carriage House with Fireplace & AC
Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Tiny farm house on horse farm
Set in a quiet cul-de-sac at the end of our driveway, this tiny house is part of our family compound and working horse farm. We have many animals. Enjoy your space, knowing we are just 50 yards away should you need anything. This is a true tiny house experience. The kitchenette has everything you need. The sleep loft is accessible by a ladder and has a low ceiling. Disclaimer there is no door on the toilet, which is tucked away in the kitchen area. WiFi connection is not guaranteed.

Zen Inspired Retreat with Private Forest Trails
Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Winery Studio w/ Private Hot Tub,Fireplace,Tasting
*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

Bedroom Forest View I Sauna I Fire-pit I Trails
Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

The Writer's Retreat: A Sweetwater Stay
Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.

Your Cozy 1 BR Apt & Relaxing Retreat
Romantic Luxury Getaway • Jacuzzi • Fire Pit • BBQ • Near Boston! Escape to this beautiful and cozy 1-bed retreat designed for comfort and relaxation. Enjoy a private jacuzzi, warm nights by the outdoor fire pit, and a BBQ grill, perfect for unforgettable moments. Located in a quiet area with easy access to Boston, restaurants, and shopping, this is the ideal stay for couples, leisure, or a peaceful weekend away.
Popular amenities for Massachusetts vacation rentals
Massachusetts waterfront vacation rentals

Spacious 2B Entire Home near Boston, Salem& Encore

“Cozy Cottage” on Great Bay

Ocean Park Retreat

Hilltown Cabin Hideaway: A River Runs Through It!

Ocean Side, Amazing View, close to town/beach, Spa

Lakefront, view of ski mtn, fireplace, sauna

Lakeside apartment, patio, hot tub, outside shower

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views
Massachusetts fishing vacation rentals

Cabin @ Newcomb Hollow Beach

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Linny's Lakeview Cottage-Updated

Lakefront House Boston, Plymouth, Cape Cod

Waterfront Spa|Hot Tub+Cold Plunge in Lake|King bd

WOW LAKE VIEW! Waterfront, Prvt Beach, King Bed!

Charming Pond-Front Boathouse

Serene Lakefront home in Cape Cod, #onlawrencepond
Massachusetts home rentals

Stone Cottage with meadow view

Cute Cottage Living by the Sea!

Large, Comfortable & Conveniently located Home

Cottage by the Sea

1BR Loft | 25 Mins to Boston | Quiet Neighborhood

Beautiful North Truro cottage with screen porch

Brooksong, the perfect Berkshires getaway

Riverfront Getaway
All about Massachusetts
Massachusetts’ bustling capital, Boston, draws in travelers seeking to explore the city’s extensive history, legendary baseball stadium, and impressive arts scene — but this northeastern state offers varied geography and options beyond its biggest city. There are opportunities for outdoor adventure, rest and relaxation, and arts and culture throughout the state. Western Massachusetts and the Berkshires is the state's rural mountain region popular with ski resorts and snow-shoeing for outdoor athletes. The towns and many farms of the central region host fall harvest celebrations and farm-to-table dining with some of the state’s best fall foliage driving routes.
Sturbridge Village is ideal for history buffs wanting a glimpse into life in New England during the 19th century. Cape Cod, a hook-shaped peninsula abou 70 miles south of Boston, is known for its beautiful beaches and lighthouses. Beachgoers and island lovers can take a ferry to the islands of Nantucket and Martha’s Vineyard for swimming, surfing, and miles of bike trails. The state’s rich maritime tradition is evident in the northern coastal towns of Newburyport, Rockport, and Marblehead.
Boston is rich in history and culture — dine at one of its award-winning restaurants or make your way through the Freedom Trail, which weaves through the city passing iconic sites of the American Revolution and gorgeous green spaces like Boston Commons and Public Garden.
What are the top things to do in Massachusetts?
Explore the History of Lexington
Drive 20 minutes outside Boston to the birthplace of the Revolutionary War. Hop on the Liberty Ride Trolley and pass multiple pivotal historical sites. Favorite stops include Lexington Battle Green — where the first shot of the Revolutionary War was fired in 1775 — and significant literary sites from classic American writers.
The Berkshires
Located on the far western border of the state, The Berkshires are popular with outdoor enthusiasts, artists, shoppers, and foodies. Known for the mountains and ski resorts here, it's a winter wonderland for skiers, snowboarders, and even offers snow tubing. Once the snow melts, you’ll find epic hiking trails, white-water rafting, and climbing opportunities abound. Towns throughout the area including Lenox, Great Barrington, Stockbridge, offer farm-to-table restaurants, antique shopping, unique musical experiences, and local theatres.
Western Massachusetts wineries
Explore picturesque vineyards while sipping on award-winning wines from dozens of wineries across Western Massachusetts. A rising star on the global wine stage, the area's wines are hand-crafted from a variety of grapes, fruits, berries, and even flowers. The region’s most common grape varieties are the vinifera varieties including chardonnay, pinot grigio, riesling, and pinot noir. Many of the wineries can be found between Amherst and Springfield with stunning landscapes to enjoy along the way.
Destinations to explore
- Beachfront rentals Massachusetts
- Rentals with a fire pit Massachusetts
- Cottage rentals Massachusetts
- Rentals with a sauna Massachusetts
- Nature eco lodge rentals Massachusetts
- Barn rentals Massachusetts
- Rentals with an accessible height bed Massachusetts
- Loft rentals Massachusetts
- Guesthouse rentals Massachusetts
- Rentals with an accessible height toilet Massachusetts
- RV rentals Massachusetts
- Rentals with a home theater Massachusetts
- Rentals with a kayak Massachusetts
- Boat rentals Massachusetts
- Rentals with lake access Massachusetts
- Private suite rentals Massachusetts
- Rentals with an EV charger Massachusetts
- Aparthotel rentals Massachusetts
- Hotel rooms Massachusetts
- Rentals with beach access Massachusetts
- Rentals with outdoor seating Massachusetts
- Family-friendly rentals Massachusetts
- Rentals with a fireplace Massachusetts
- Mansion rentals Massachusetts
- Rentals with a patio Massachusetts
- Beach house rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Rentals with breakfast Massachusetts
- Farmstay rentals Massachusetts
- Rentals with a hot tub Massachusetts
- Resort rentals Massachusetts
- Waterfront rentals Massachusetts
- Luxury rentals Massachusetts
- Bungalow rentals Massachusetts
- Ski-in/ski-out rentals Massachusetts
- Lakehouse rentals Massachusetts
- Pet-friendly rentals Massachusetts
- Tiny house rentals Massachusetts
- Campsite rentals Massachusetts
- Smoking-friendly rentals Massachusetts
- Vacation home rentals Massachusetts
- Condo rentals Massachusetts
- House rentals Massachusetts
- Villa rentals Massachusetts
- Rentals with pools Massachusetts
- Apartment rentals Massachusetts
- Rentals with a washer and dryer Massachusetts
- Chalet rentals Massachusetts
- Serviced apartment rentals Massachusetts
- Bed and breakfasts Massachusetts
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- Things to do Massachusetts
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