Vacation rentals in Massachusetts Bay

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Top-rated vacation rentals in Massachusetts Bay

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Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 106 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Mar 23 – 30

G$21,026 GYD per night

Guest favorite

Loft in Abington

4.99 out of 5 average rating, 119 reviews

Modern, Naturally lit Loft

Enjoy a quiet getaway, with private entrance, in a private loft apartment situated in South Shore, MA. The loft is a large, open floorplan flooded with natural light. Enjoy nature walks at the Abington/Hanover rail trail for a great morning walk or a nice evening on the private balcony. There is a full-size kitchen in the loft at your disposal. We have a parking space in front of the house, fast WIFI, and a designated desk for work if you need it. This loft Is amazingly comfortable and peaceful!

Dec 7 – 14

G$26,156 GYD per night

Guest favorite

Cabin in Cohasset

4.92 out of 5 average rating, 285 reviews

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.

Oct 7 – 14

G$32,767 GYD per night

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a sought after cape style cottage community. It offers a Private Association Beach. The cottage has water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. You can also Walk, Bike, or Fish on Cape Cod Canal. Close to restaurants, hiking trails, Mass Maritime, and Water Wizz. Location! 5 min Cape Cod Bridge. 20% off wk.

Oct 7 – 14

G$23,097 GYD per night

Guest favorite

Guest suite in Salem

4.99 out of 5 average rating, 694 reviews

The Mason Suite of Salem

*We have THE BEST location in all of Salem! Take a look at our reviews!* The Mason Suite is a boutique lodging experience with all the comforts of home! Built in 1844 and nestled among Salem's most prized architecture, the Suite is just steps from the Witch Museum, bustle of the pedestrian mall, and Salem Common! Recently renovated from top to bottom! You'll be surrounded by fine furnishings, culture and history! The location is 10/10! We strive to provide you with the ideal Salem experience!

Apr 23 – 30

G$30,487 GYD per night

Guest favorite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette and an outdoor space with a fire pit and charcoal grill. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

Oct 28 – Nov 4

G$29,775 GYD per night

Guest favorite

Guest suite in Marblehead

4.92 out of 5 average rating, 245 reviews

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Dec 10 – 17

G$23,917 GYD per night

Guest favorite

Guesthouse in Cohasset

4.98 out of 5 average rating, 106 reviews

Lovely 1 Bedroom Guest House. Downtown Cohasset

Lovely guest house. Newly renovated, nicely furnished & clean. Spacious living room/dining room with fully equipped kitchen. Large 1 bedroom & 2 full baths. Convenient location--walk to downtown, harbor, restaurants, churches and the Common. Train to Boston"s South Station 5 min away. Cohasset is the quintessential New England seaside village located on the South Shore of Massachusetts between Boston and Cape Cod. Host lives next door on property.

Oct 6 – 13

G$41,159 GYD per night

Guest favorite

Home in Lynn

4.91 out of 5 average rating, 227 reviews

Clean, spacious In-Law Suite -Near Everything

Immaculately furnished, clean and spacious In-Law Suite features: 1 bedroom, 1 full bath, dining kitchen, and living room located steps from Lynn Woods Reservation (over 30 miles of picturesque New England trails perfect for hiking, running, mountain biking and cross-country skiing) and short drives from beaches, Boston and North Shore. Kids toys, a baby crib and access to a large beautiful upstairs deck and bbq are available upon request.

Feb 5 – 12

G$30,379 GYD per night

Guest favorite

Guest suite in Rockport

4.99 out of 5 average rating, 611 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Apr 10 – 17

G$26,255 GYD per night

Guest favorite

Home in Quincy

4.96 out of 5 average rating, 124 reviews

Artist's Haven (2)

Before booking, please conduct thorough research on Quincy, MA, to ensure it aligns perfectly with your needs. As a dedicated Superhost, I'm committed to earning your 5-star review. My home offers easy check-in with a keypad entry. The cozy second-floor one-bedroom has a private entrance, spa-like bathroom, well-equipped kitchen, queen-sized bed, 55" TV, high-speed WiFi, and on-site parking for one car.

Jul 21 – 28

G$24,155 GYD per night

Guest favorite

Guest suite in Scituate

4.91 out of 5 average rating, 175 reviews

Private Scituate Getaway - walk to harbor

Delightful studio apartment with private entrance off historic First Parish Road. Located a mile from Scituate Harbor, beaches, restaurants, golf course, movie theater, shops, and Greenbush train into Boston. Space includes comfortable queen-sized bed, full bathroom, sofa, cable TV and wifi. Additional amenities include ceiling fan, air-conditioning, mini-fridge, Keurig, and microwave.

Jun 24 – Jul 1

G$42,281 GYD per night