Vacation rentals in Winthrop

4.87 out of 5 average rating, 109 reviews

A serene morning on the lake is depicted, with two individuals paddling a kayak through mist-covered water. The surrounding landscape features dense trees and gentle hills, while soft light reflects off the calm surface, creating a peaceful atmosphere.

Vacation home in Natick

Private Lakefront with game room/Newly renovated

Ideal private location on crystal clear Lake Cochituate! Peaceful quiet spot w amazing view only 20 min to Boston & 1 or 2 min drive to anything u could need Fun game room &free use of tandem kayak & paddleboard and fishing Sliding barn door separates main king bedroom, bath, & open kitchen & livingroom from the back 2 queen beds, game room & bath Im always available to answer questions + provide tips, but I also respect your privacy & want u to feel comfy & independent 》25 6 person 3 car limit

4.97 out of 5 average rating, 265 reviews

The charming entrance of the cottage is framed by vibrant greenery and colorful flowers. Two wooden chairs are positioned in front of the entrance, welcoming guests. A decorative flag flutters above the door, completing the inviting scene.

Guesthouse in Annisquam

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

4.96 out of 5 average rating, 307 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

4.95 out of 5 average rating, 22 reviews

A sandy beach extends along a calm ocean, where gentle waves lap at the shore. Rocky formations are visible in the water, and a clear blue sky overhead enhances the serene coastal view.

Home in Scituate

Button Beach Cottage

Capture the breeze of the coast at Button Beach Cottage! •5 min walk to beach. •Brand new remodel. •Family friendly. •Oceanview balcony. •Luxury bunk room. •Dedicated workspace. •Outdoor dining area on spacious deck directly off kitchen. •Access to lifeguard beach Primary BR: king bed, TV, reading nook, ocean view & balcony. BR #2: queen bed, dedicated work space, ocean view & balcony. Bunk room: 5 twin beds with play space. Full bath on each floor. Tub, standing shower, washer & dryer.

Condo in Lakeside Marblehead

An expansive view of the harbor is captured, showcasing numerous sailboats anchored in the water. Lush green grass and wooden benches frame the scene, with a flagpole standing nearby. A large tree casts shade on the area, contributing to a peaceful atmosphere.

4.99 out of 5 average rating, 175 reviews

Harbor Hideaway

A uniquely detailed single-floor unit in a 2 unit house featuring a large kitchen/dining room, living room, and a private cozy veranda. Queen Bedroom & additional sleeping for 2 with a deluxe air mattress. This space is perfect for couples, families with young children, or a single person. Only one dog allowed no cats. This unit is on the lower floor of a two-family house occasionally you can hear steps from the upstairs. PLEASE note parking on site is very tight small cars compact SUVs only.

4.98 out of 5 average rating, 380 reviews

A multi-story coastal home is seen from a rocky shoreline, surrounded by lush greenery. Several white Adirondack chairs are positioned on the patio, enhancing outdoor relaxation. The gray exterior of the house features a large balcony with white railings, blending harmoniously with the natural landscape.

Apartment in Salem

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.

4.86 out of 5 average rating, 113 reviews

An aerial view captures the scenic coastline and sandy beach lined with boats. A variety of residential buildings dot the landscape, interspersed with greenery. The neighborhood showcases the charm of coastal living, with the sea and a pier visible in the background.

Apartment in Swampscott

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

4.97 out of 5 average rating, 118 reviews

Home in Gloucester

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

4.84 out of 5 average rating, 61 reviews

The image captures a serene beachfront with gentle waves lapping against sandy shores. Rocks line the edge of the beach, while a clear blue sky stretches overhead, merging with the tranquil sea. The distant coastline features various structures, enhancing the scenic view.

Home in Scituate

Sand Hills Barker Tavern RiverClub lighthouse -

Walking distance to sand hills beach - super close to BARKER TAVERN! One mile from center of town with restaurants and shops. Nearby basketball court. Grassy backyard . New furnishings new full bath and new mattresses. Freshly painted well maintained by owner bedrooms are upstairs. There is only one full bath upstairs Totally redone 2024. Bungalow beach style home. some guests find stairs to be “ steep” … my 82 year old mom does fine with the stairs and rail!

5 out of 5 average rating, 22 reviews

Home in Scituate

Coastal Retreat

Welcome to our coastal rental, a charming retreat nestled in the heart of a vibrant beach town. With modern amenities and coastal decor, unwind in the light-filled spaces and savor beautiful marsh views from the well manicured backyard. Located about a mile from Main Street, you can walk or bike on the flat sidewalk to restaurants, shops and the harbor. Close by you'll also find a dog park, the beautiful public golf course, Widow's Walk and of course the beach!

4.96 out of 5 average rating, 102 reviews

A well-maintained outdoor area is highlighted, featuring a grassy lawn leading up to stone steps. The house, adorned with dark siding, is framed by a large tree and offers a welcoming seating arrangement on the porch. Clear skies provide ample natural light.

Condo in Gloucester

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

4.95 out of 5 average rating, 174 reviews

The living area features a stone fireplace and a flat-screen television mounted above. The space includes a mix of comfortable seating, such as a blue sofa and patterned armchairs. Exposed wooden beams and a spiral staircase add architectural interest to the cozy environment.

Cottage in Stow

White Pine Cottage

Cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are visiting the area. Located in quiet neighborhood with very little traffic. Convenient to local farms, orchards, golfing, parks and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

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Popular amenities for Winthrop vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Winthrop's top sights

Harpoon114 locals recommend

Belle Isle Seafood9 locals recommend

Constitution Beach3 locals recommend

Deer Island22 locals recommend

Cafe Rossetti's6 locals recommend

Blackstrap BBQ8 locals recommend

Other great vacation rentals in Winthrop

4.88 out of 5 average rating, 104 reviews

Home in Ipswich

Hillside Ocean View 2BR with Private Beach Access

4.98 out of 5 average rating, 195 reviews

A fire pit is surrounded by colorful adirondack chairs in a grassy area, with bright yellow flowers adding a pop of color. The view in the background includes a landscape of greenery leading to the water, suggesting a peaceful outdoor space for gatherings.

Home in Ipswich

Stagehill Beach House

4.86 out of 5 average rating, 84 reviews

A serene park scene is shown, with a sandy area leading to a calm body of water. People can be seen enjoying various activities under a partly cloudy sky, framed by lush greenery and large trees. A sign for Arlington Recreation is prominently displayed.

Guest suite in Arlington

★Modern Studio-Private Entrance,Washer+Dryer★

4.91 out of 5 average rating, 123 reviews

Home in Gloucester

Gloucester Beach House, near Good Harbor Beach!

4.98 out of 5 average rating, 41 reviews

A full moon casts a golden glow over the water, illuminating the surface with shimmering reflections. In the background, two large houses with red roofs are visible, set against a twilight sky.

Apartment in Swampscott

Ocean View Apartment 2nd Floor

5 out of 5 average rating, 8 reviews

A serene beach scene is captured under a clear blue sky, with gentle waves lapping against the shore. The radiant sun reflects off the calm water, creating a sparkling effect. Smooth rocks line the edge of the beach, adding natural texture to the landscape.

Home in Marshfield

Home by the sea

4.81 out of 5 average rating, 21 reviews

Apartment in Cambridge

Elegant 3-Bed Oasis in Cambridge Near Harvard/MIT