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Holiday houses in Middleton

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Top-rated holiday rentals in Middleton

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

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Top Guest favourite
The entrance to the property is framed by lush greenery and flowering plants. A welcome path leads to the front door, which is placed under an overhang, creating a gentle entryway into the inviting space.
Guest suite in Danvers
4.97 out of 5 average rating, 108 reviews

The sweet suite

Ground level. Spacious room with a King Bed and a bonus smroom with a ( twin pull out bed) couch and desk/vanity. The sizeable bathroom is freshly remodeled. Kitchenette has a small sink, refrigerator and microwave. It is in a quiet neighborhood only minutes from a rail trail, route 62, interstate 95 route 1 and route 128. Off Street parking. We are 5 miles to Salem Mass, 44 miles to New Hampshire, 77 miles to the cape cod canal, 19 miles to Boston. We are 4 miles to the Beverly train Station.

Guest favourite
Home in Wakefield
4.82 out of 5 average rating, 111 reviews

Beautiful home next to train to Boston, near Salem

Boston and Salem location, 3-story condo in two-unit building with its own entrance. Kitchen is brand-new, with a large bar area and all the appliances. One bedroom with a king-size bed is located on the main 2nd level. Two bedrooms upstairs, with one King bed and one Queen bed. It is located within walking distance to the Wakefield commuter rail with trains running into downtown Boston. Also, adjacent to a walkable park around a stunning lake, and a small downtown with stores and restaurants.

Top Guest favourite
The airy living space features large windows offering panoramic sunset views. A dark sectional sofa and a roll-top desk are strategically placed, complemented by a stylish area rug. Soft lighting enhances the inviting atmosphere, further accentuated by tasteful artwork on the walls.
Condo in Peabody
4.94 out of 5 average rating, 108 reviews

Peabody Penthouse Top of the World Sunset View

Enjoy sunrise/sunset panoramic view from the new 6th floor Penthouse Sanctuary, the highest point in Peabody! This thoughtfully decorated spacious Penthouse open floor plan is a place to retreat, recharge, write, envision, and to enjoy the best of life. A walk away from the NS Mall/Borders Books where the Logan Express arrives. Also a mile away are the running trails, lovely ponds and apple picking at the city run Brooksby farm and six miles away from historic Salem. You will love it here!

Top Guest favourite
A warm and inviting master bedroom is visible, featuring a queen-size bed and a cozy sofa facing a stone fireplace. An antique trunk serves as a unique side table. Natural light filters through the windows, illuminating the wooden ceiling and floor.
Guest suite in Peabody
4.95 out of 5 average rating, 642 reviews

PRIVATE, LARGE COUNTRY STYLE SUITE

LARGE ground floor apartment with your own entrance. Master Bedroom has: . Half bath . Queen size bed. . Full size sofa bed . TV/Netflix . Cozy gas burning heating stove . Desk/chair . Water cooler . Coffee/Tea Kitchen includes . Sink . Big Refrigerator . Microwave . Induction stove tops . Toaster Oven Living Room . Queen Sofa Bed . 2 Recliners . 50" TV Laundry Room Full Bathroom Shopping plaza 2 miles down the road and just 5 minutes to I- 95 or Rt. 1 and only 20 minutes to Boston or Salem.

Guest favourite
The exterior of a two-story home is shown, featuring beige siding and multi-pane windows. A well-maintained front yard includes patches of grass and decorative bushes. A staircase leads to the front porch, with a fenced yard visible in the background, surrounded by trees for added privacy.
Home in Georgetown
4.81 out of 5 average rating, 220 reviews

Nothing Fancy Older Pet Friendly Home – near I-95

Enjoy your very own country living retreat! Our pet friendly home sleeps 8 with a large fenced in yard, so bring the kids & furry friends. There is a big backyard and lots of trees providing privacy. The fence is older but secure enough for your pets. Guests please know this is an older house inside. The finishes are older and cheaper. We are 1 min from I-95 & within 15 minutes of restaurants, golf course, & wedding venues. Guests that are very sensitive to smell should not book this place

Top Guest favourite
Guest suite in Topsfield
5 out of 5 average rating, 63 reviews

private suite w/king bed

Enjoy a comfortable stay in our private and spacious sun-filled loft. Nestled on a scenic hill in a beautiful corner of Topsfield, this cozy studio suite is 30 minutes from Boston; 25 minutes from Salem; less than 20 minutes from local beach towns, Endicott College and Gordon College; and approx. five minutes from the Topsfield Fair Grounds, the Ipswich river, Mass Audubon hiking trails, and wedding venues like Peirce Farm at Witch Hill, The Commons 1854, Willowdale Estate and Moraine Farm.

Top Guest favourite
Apartment in Woburn
4.88 out of 5 average rating, 104 reviews

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

Guest favourite
Farm stay in North Andover
4.94 out of 5 average rating, 176 reviews

Winery Bungalow: Private 2-Story Home+Wine Tasting

Our 2-story Bungalow is ideal for couples, friends, or professionals seeking a relaxing retreat. The space features a spacious living/kitchen area and full bath upstairs, a large bedroom downstairs, in-unit laundry, and additional dining and lounge seating on the enclosed porch. The entrance is through a gate and up a set of stairs, and there are also stairs inside the unit. Booking includes a wine tasting and 10% off wine purchases. Please review all details and photos prior to booking.

Top Guest favourite
Home in Danvers
4.98 out of 5 average rating, 112 reviews

Large, Comfortable & Conveniently located Home

You will be close to everything when you stay at this centrally-located private, updated historical home. 4 bedrooms & 2 baths w/plenty of extra space for large families or groups. Fenced-in spacious patio with huge backyard. Sizable, private parking area. Near Routes 95 & 128. Only 25 mins to Boston. Perfect for trips to picturesque points, including Boston, Gloucester, Newburyport, Rockport, Cape Ann, historic Salem & Maine coastal towns and cities. Dog friendly.

Guest favourite
Guest suite in Peabody
4.97 out of 5 average rating, 232 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 with a microwave and Keurig coffee. 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.

Top Guest favourite
An open-concept living space features a modern grey sectional couch and a contrasting black coffee table on a colorful rug. Custom olive green bookshelves are filled with decor and books. A staircase leads to a well-lit area, enhancing the spacious atmosphere.
Apartment in Peabody
4.95 out of 5 average rating, 143 reviews

Modern Apartment - Easy Commute to Salem/Boston

This modern, spacious and cozy home was completely renovated at the end of 2022, thoughtfully designed for our family and guests when they visit. It is conveniently located close to popular spots such as Salem, North Shore and Boston (right off route 1 and highway 95). Grocery store, pharmacy, dry cleaners and other amenities are just down the road. In a quiet and friendly neighborhood. We open it up for Airbnb guests seasonally. We look forward to hosting you!

Guest favourite
A cozy living space features a light-colored sectional sofa in front of a wall-mounted television. A framed artwork decorates the white walls, and a small round table sits between a patterned area rug and the sofa, adding comfort to the setting.
Apartment in Stoneham
4.87 out of 5 average rating, 384 reviews

Entire guest suite in Stoneham

Come enjoy this quiet and comfy home in the heart of Stoneham—your perfect getaway just 20 minutes from the airport and the historic city of Boston. Conveniently located near shopping malls, restaurants, coffee shops, grocery stores, and the natural beauty of Middlesex Fells Reservation and Stone Zoo, this peaceful retreat is designed to make your trip relaxing, enjoyable, and stress-free.

Popular amenities for Middleton holiday rentals

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Essex County
  5. Middleton