Guesthouse vacation rentals in Massachusetts

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Top-rated guesthouses in Massachusetts

Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

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Guest favourite

Guesthouse in Barnstable

5 out of 5 average rating, 132 reviews

Modern Fireplaced Carriage House with Beach Permit

Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

Guest favourite

Guesthouse in Northampton

5 out of 5 average rating, 322 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Guest favourite

Guesthouse in North Adams

5 out of 5 average rating, 243 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Guest favourite

Guesthouse in Amesbury

4.95 out of 5 average rating, 114 reviews

Two Penny Loft at Amesbury Farmhouse - Guest Suite

This cozy 2 story guest suite w/separate entrance and deck, is part of a large 200 year old Amesbury farmhouse set on a peaceful 3 acre lot. The first floor contains a comfortable living/dining area, along with small charming bathroom. Upstairs is a large bedroom with vaulted ceiling, skylights, king-sized bed and sitting area. Amesbury is steeped in history and guests will be close to amazing breweries, restaurants, historical sites, shops, galleries, walking trails, lakes, beaches and more!

Guest favourite

Guesthouse in Scituate

4.92 out of 5 average rating, 103 reviews

Serenity House

Take a deep breath while relaxing on this 1+ acre wooded estate surrounded by the Hubbell Woodland Preserve and the Hatherly Golf Course across the street. Walk along seaside estates that greet you on your way to swim at Minot Beach which is a short walk away. Ride your bike to Cohasset Harbor while taking in the view of the fishermen catching lobsters and have dinner at the local restaurants. Listen to the waves and smell the salty ocean air and relax and sleep peacefully at Serenity House!

Superhost

Guesthouse in Bourne

4.78 out of 5 average rating, 155 reviews

Rustic Carriage House by the Sea

This is an authentic small old Cape Cod rustic carriage House. Which is charming, antique and unique. It is in a beautiful one-of-a-kind location. Loaded with cozy fun. A great getaway any time of the year! The Carriage house is walking distance away from beautiful Hens cove and is near many activities, Bike paths, the canal, the ferry, hiking, fishing, and many restaurants. Great for pet friendly Families, a couple of couples, friends that want to stay together, and bigger groups.

Guest favourite

Guesthouse in Lenox

4.91 out of 5 average rating, 198 reviews

Modern Barn with Loft at House on Golden Hill

Featuring 35 foot cedar ceilings, large windows, and skylights, The Barn is an oversized two-bedroom apartment with loft at House on Golden Hill, a 1790's farmhouse property in Lenox. The Barn is a detached dwelling with large secluded outdoor space and reserved parking for 3 cars. Situated next to the property's river, the barn provides sweeping mountain views and an idyllic Berkshires experience. Centrally located in the Berkshires and minutes from downtown Lenox and Tanglewood.

Guest favourite

Guesthouse in Northampton

4.93 out of 5 average rating, 262 reviews

Large Studio – Walk to Town

IMPORTANT: Please read the full description about the eco-friendly policy and click the "CONTACT HOST" button, rather than making a reservation. I will respond very quickly to your request. Thank you for your consideration! A unique studio, loft-like, surrounded by beautiful gardens, a short walk to downtown and Smith College; perfect for visiting the five colleges, attending weddings, graduations, workshops, writing and research; close to hiking and bicycle trails.

Guest favourite

Guesthouse in Westminster

4.98 out of 5 average rating, 362 reviews

Guest House - 4 miles from Wachusett Mt.

Enjoy your stay in this cozy, newly renovated semi-attached in-law unit. It is located close to Route 2, walking distance to the town center, only 4 miles from Mt. Wachusett in a quiet neighborhood. It has 2 parking spaces and a private entrance. This unique space has everything to make you feel at home – including WiFi and Netflix. The kitchen is equipped with a Keurig Coffee Maker, Mini Fridge, and a Microwave. Queen-size bed, fresh towels, body wash are also provided.

Superhost

Guesthouse in Dartmouth

4.88 out of 5 average rating, 120 reviews

Lovely Lakeside Cottage

Keep it simple at this peaceful and centrally-located cottage. Lovely lakeside cottage with open floor plan. Centrally located in southeastern Massachusetts with short drives to Boston, Providence, Newport, and Cape Cod. Several beaches within 20 minutes. Washer/ Dryer on site and California King Size bed. A simple five (5) minute ride to UMass Dartmouth. Cottage has a living room, full kitchen, bedroom, full bath, and small dining area.

Guest favourite

Guesthouse in Amherst

4.95 out of 5 average rating, 549 reviews

Cozy get-away!

This quiet option is less than two miles from the center of downtown Amherst, a thriving college town with museums, libraries, small stores, restaurants for every budget, hiking trails galore. We offer a relaxing space in a friendly, safe, residential neighborhood. Five minute walk to 2 bus stops. If you are looking for some privacy with access to western Mass., you've found it!

Guest favourite

Guesthouse in Framingham

4.97 out of 5 average rating, 249 reviews

Private guest house on beautiful country road

Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.