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, 127 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
A spacious living area is highlighted by framed windows that provide ample natural light and offer views of the sky. A modern couch and an antique roll-top desk are present, accompanied by a cozy armchair. A decorative star design in the area rug adds a unique touch.
Condo in Peabody
4.94 out of 5 average rating, 119 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
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, 654 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 charming guest suite is visible amidst a well-kept yard, characterized by a blend of unique architectural elements. The structure features multiple windows and a welcoming entrance. Surrounding greenery and trees provide a sense of tranquility, enhancing the inviting outdoor space.
Guest suite in Beverly
5 out of 5 average rating, 135 reviews

Peaceful, 1888 Mediterranean Manor by the Beach

Architectural charm in this newly renovated, eco-friendly guest suite, could be a destination in itself with a granite kitchen, open living/dining, large yard, patio, private outdoor fireplace and fountain, and brick courtyard. A block away are beaches, lighthouse, playgrounds and a seaside park. Beverly has historic theatres, top-notch dining, cafes and microbrews. Boston is conveniently 30 mins away; other attractions like museums, castles, trails, water sports and whale watching are nearby.

Top guest favourite
Apartment in Woburn
4.95 out of 5 average rating, 242 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

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, 75 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.

Guest favourite
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
4.88 out of 5 average rating, 144 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 well-lit sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light fills the room from multiple windows, complemented by a cozy seating nook and shelving that adds a charming touch to the serene atmosphere.
Apartment in Salem
4.98 out of 5 average rating, 447 reviews

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

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, 297 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
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, 130 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, 145 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
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