Vacation rentals in Middleton

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Top-rated vacation rentals in Middleton

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

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Top guest favourite
A well-maintained single-story house is framed by vibrant trees and greenery. The exterior features a welcoming porch with white columns. A lush lawn with seasonal foliage appears in the foreground, and a rainbow can be seen arching across the sky.
Guest suite in Danvers
4.98 out of 5 average rating, 126 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.

Top guest favourite
The exterior of the building features a light-colored facade, with red shutters accentuating the windows. A well-maintained garden area includes a small tree and seasonal decorations, including a pumpkin. A white garage door is visible to the left, and steps lead to the entrance.
Guest suite in Peabody
4.95 out of 5 average rating, 652 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.

Top guest favourite
A spacious loft area is highlighted by vaulted ceilings and numerous windows, allowing natural light to fill the space. A comfortable king-sized bed is paired with bedside lamps. A cozy seating arrangement includes a sofa and an armchair, with a wooden coffee table at the center.
Guest suite in Topsfield
5 out of 5 average rating, 73 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.

Superhost
A modern kitchenette is featured with stainless steel appliances, including an oven and refrigerator. A spacious gray sectional sofa is positioned on a geometric patterned area rug. Bright windows allow natural light to illuminate the room, complemented by decorative mirrors and a potted plant.
Apartment in Woburn
4.87 out of 5 average rating, 143 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!

Top guest favourite
A framed artwork features the silhouette of a raven against a shimmering gold background. The ornate frame adds a touch of elegance, enhancing the gothic decor of the space.
Condo in Salem
4.95 out of 5 average rating, 111 reviews

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

Guest favourite
The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.
Farm stay in North Andover
4.95 out of 5 average rating, 296 reviews

Winery Studio w/ Private Hot Tub & Wine Tasting

Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

Top guest favourite
An outdoor patio area is illuminated with string lights, featuring a seating arrangement with a sectional sofa and a dining table surrounded by black chairs. A grill is located nearby, and a decorative border of gravel and plants enhances the space.
Apartment in Salem
4.93 out of 5 average rating, 147 reviews

Newly renovated apartment close to downtown.

Newly renovated apartment walking distance from downtown Salem. Enjoy the privacy of your own apartment with plenty off street parking only 1 mile from the heart of downtown Salem and less than a mile from the commuter rail. There’s also a neighborhood market with beer/wine and some groceries 1 minute walk from the apartment. Plenty of street parking. Take a 5 minute Uber ride or 15-20min walk into downtown Salem and enjoy its rich history. Easy access to Rt. 128 and Rt. 1.

Top guest favourite
A large tree with a broad canopy dominates the lush backyard, surrounded by greenery. The area features a stone border outlining a patch of grass, with glimpses of the landscape beyond, including wooded areas and a play structure in the distance.
Home in Danvers
4.98 out of 5 average rating, 129 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.

Top guest favourite
A spacious living area features a modern sectional couch and a grey accent chair, with an area rug adding warmth. Custom-made olive green bookshelves showcase a variety of decorative items. The open layout leads towards a staircase and kitchenette, enhancing the inviting atmosphere.
Apartment in Peabody
4.95 out of 5 average rating, 144 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!

Top guest favourite
A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.
Home in South Berwick
5 out of 5 average rating, 137 reviews

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Top guest favourite
A light-filled living area features a soft blue sofa adorned with cushions in vibrant colors. Large windows offer views of the serene water outside, while greenery and a stylish glass coffee table enhance the inviting atmosphere.
Guest suite in Beverly
4.99 out of 5 average rating, 110 reviews

Shoreview Studio Lounge

This historic Victorian residence, is today host to this seaside studio lounge. Once inside, you’ll fall captive to the seascape off Independence Park. The Atlantic panorama provides an awe-inspired sunrise daily. From its elevated perch, the studio has a contemporary feel with its private observation deck to its sophisticated lighting and wet bar design. Comforts include heated floors, air conditioning and powered room-darkening blinds.

Top guest favourite
Apartment in Danvers
5 out of 5 average rating, 28 reviews

Salem nearby | Petite retreat

Welcome to your cozy getaway! This apartment offers a blend of comfort & charm w a 1 bedroom, full kitchen & living area. Located on the top floor, enjoy nature views in a peaceful retreat w free parking. A prime spot just a short ride to downtown Salem where you can explore the city’s historic sites, waterfront & dining scene. This is a great home base for your North Shore adventure for a weekend escape or an extended stay!

Popular amenities for Middleton vacation rentals

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