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

SamanthaRating, 5 stars3 weeks ago

My family of six was extremely pleased with our stay at Dean’s property. He was incredibly responsive and helpful when I was having trouble making the reservation. The home was exactly as described. Very clean. Plenty of linens and towels. My kids loved the game room. Would definitely stay here again.

4.96 out of 5 average rating, 302 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

StephanieRating, 5 stars4 weeks ago

Frank went above and beyond to communicate check-in instructions, rules of the Air BnB, had all the thoughtful amenities for a slumbo! Definitely an ideal location for nicer weather with the location! Unfortunately the weather hindered the ability to fully enjoy this experience with the water so close! Would book again with better weather!!!

4.83 out of 5 average rating, 323 reviews

A serene outdoor seating area is surrounded by lush greenery, featuring two dark wooden chairs and a small table. A natural landscape includes a gently flowing brook nearby, with a weathered bench positioned to enjoy the peaceful view.

Home in Plymouth

Historic 1 Bed/In Town/Best Location/Hot tub/deck

LiviaRating, 5 stars4 weeks ago

I had an amazing stay! The place was clean, well-organized, and had everything we needed. The location is great, just a short walk to lots of restaurants and coffee places, making it easy to explore. All the pictures are accurate. Highly recommend!

4.84 out of 5 average rating, 111 reviews

An outdoor seating area features bright orange Adirondack chairs arranged around a fire pit, complemented by a shaded area provided by a large umbrella. The cottage is visible in the background, showcasing its coastal charm with fresh landscaping enhancing the inviting space.

Cottage in Newbury

Designer decorated-Sunset Bliss- Beach 3 min walk

MattRating, 5 stars5 months ago

Staying in this guest house was really great for me, my wife and our two small dogs. The front of the home overlooks are beautiful marsh. The area is very peaceful, and it's next-door to a quaint little park, and a few minutes walk to a private beach.

4.95 out of 5 average rating, 21 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

DennisRating, 5 stars4 days ago

Courtney & Chris were amazing hosts! They went above and beyond to answer all our concerns prior to our stay regarding public transport to Boston for the marathon. The house was awesome, with the beach only blocks away. We had an excellent experience & we're so grateful for our hosts and this beautiful lodging.

4.87 out of 5 average rating, 111 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

AnissaRating, 5 stars3 days ago

We absolutely loved our stay at Ryan’s place! The home was beautiful, spacious, and pristine—just like the photos. Ryan was a wonderful host from booking to check-out, making everything easy and welcoming. We especially loved the location, with the beach and great local restaurants just a short walk away. We would definitely stay here again!

5 out of 5 average rating, 14 reviews

The modern kitchen features granite countertops and stainless steel appliances. Ample cabinetry provides storage, with a central wooden island offering additional workspace. Natural light enters through the window above the sink, highlighting the clean lines and functional layout of the space.

Home in Rockport

Adorable renovated house, steps from Front Beach

EmilyRating, 5 stars7 months ago

Gretchen’s house is a charming, two-story one on a very nice and quiet little street. The furnishings are pretty and tasteful, and there is comfortable living room furniture, as well an excellent beds and pillows. Our favorite thing was its location, within very easy walking distance from a gorgeous park and beach. Downtown was also reachable via a short walk. We did some of our own cooking and found everything we needed. Gretchen was an especially nice and responsive hostess. If we were lucky enough to get to Rockport again, I would want to stay there.

4.83 out of 5 average rating, 60 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 -

KimberlyRating, 5 stars1 month ago

Stayed here with a few of my friends for a wedding and the place was perfect! Really close to the Barker House wedding venue, walkable to downtown Scituate. Beds were very comfy and the place was very clean. Overall, a great stay!

5 out of 5 average rating, 20 reviews

A harbor scene features numerous boats docked alongside wooden piers, with a small fuel dock prominently situated at the center. Lush greenery surrounds the area, and a soft, golden light fills the sky as the sun sets, creating a serene atmosphere.

Home in Scituate

Coastal Retreat

RachelRating, 5 stars3 months ago

Our stay at this lovely Scituate Coastal Retreat was fabulous. The house was immaculately clean and the decor was perfection. The common areas were cozy, but spacious and the kitchen was well stocked with any tools/utensils we needed. Beds were comfortable and our party of 4 adults had plenty of room. The hosts left great suggestions for local dining and the house was only a 2 min drive (15min walk) to downtown Front St restaurants and shopping. Host Andrew was very responsive and wonderfully accommodating, allowing for a later check-out when requested. We were staying in the Winter, so perhsps check out time may not be as flexible in the warmer months. Check-in & check-out was a breeze! We hope to rent this property again. Thank you Andrew & Madeline!

5 out of 5 average rating, 4 reviews

An aerial view of a spacious two-story house surrounded by lush greenery. The well-maintained exterior features a pitched roof, large porch, and expansive yard. The nearby coastline is visible in the distance, highlighting the peaceful residential neighborhood.

Home in Rockport

Experience Classic New England-walk to beach&shops

CamaiRating, 5 stars1 day ago

This house is perfect for the space / location. Not many listings with hot tub and still with great distance to things/beach. A very family friendly space / very ideal for large/multi family based on the kitchen/dining and outdoor areas. Note he is also transitioning/updating furniture which I think will help a lot.

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What guests are saying

Cottage/Loft Combo!|Deck|Sleeps 7|2 Parking Spaces

5 out of 5 average rating, 4 reviews8 months ago

My family and I have been visiting Rockport every year for the past 30 years. We have rented many places over that time, and this was one of the nicest! We really appreciated the welcome message and pastries upon our arrival. We stayed in the cottage and the loft, which both were very clean and nicely decorated with comfortable beds. We were very thankful for the air conditioning as it was a VERY hot week. Check in was straight forward and easy. Parking was a little far away but allowed for a place to park when downtown was busy. Alexander was top notch and extremely responsive. I would definitely stay there again!!!

Home in Rockport

What guests are saying

Bearskin Neck oceanfront w/ 2 parking spots!

4.97 out of 5 average rating, 61 reviews2 days ago

Location, location, location!! Gorgeous views, ocean breezes, and easy walking to shops and restaurants. We had a great time exploring the area and loved the beach cottage vibe. Aine was a perfect host, and made sure we had everything we needed. Would ABSOLUTELY stay here again.

Cottage in Rockport

What guests are saying

Village Colonial with Cohasset Harbor Views

4.91 out of 5 average rating, 32 reviews3 weeks ago

This is a beautiful and spacious home with New England charm and in a great location. The house looks exactly as pictured and was spotless. The rooms were well appointed with lots of space to sit and relax. It’s perfect for visiting this beautiful area of MA. Michael is a responsive and helpful host and very considerate of his guests. We would absolutely stay again and can highly recommend this home for your stay. Five star all the way.

Home in Cohasset

What guests are saying

#1 Top Flr Waterview|Lux Design|Pvt Balcony

5 out of 5 average rating, 33 reviews2 days ago

This was my third time at Darryl’s‘s place and I will be back again. For the simple fact that if you need to be in the Beverly and Salem area this is a perfect location to post up and walk to everything you need. Or, drive if you must. There’s a train to Boston a couple blocks away.Darryl‘s place itself has everything you need to feel and operate like you’re at home. See you again soon, Darryl.

Apartment in Beverly

What guests are saying

3BR home in town w/ ample parking + lush garden

4.88 out of 5 average rating, 8 reviews7 months ago

Abby's home was gorgeous, felt personal unlike many airbnbs that are clearly only for guests to stay, and was so spacious. This was one of the few airbnbs that I can remember that had all of the kitchen supplies we needed for our admittedly limited use. Abby was so communicative and the location was excellent, only being a few minutes away from downtown Rockport. I would recommend this place for anyone!

Home in Rockport

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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

Antique Table Restaurant43 locals recommend

Belle Isle Seafood27 locals recommend

Constitution Beach26 locals recommend

Deer Island22 locals recommend

Cafe Rossetti's20 locals recommend

Other great vacation rentals in Winthrop

4.77 out of 5 average rating, 154 reviews

A serene waterfront view showcases a calm pond surrounded by trees in autumn colors. An inviting sandy beach area features bright blue adirondack chairs and a kayak resting on the shore, reflecting a peaceful outdoor setting.

Condo in Plymouth

Clear Pond Pet Friendly Inn

NicklausRating, 5 stars5 months ago

Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.

4.95 out of 5 average rating, 171 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

NickRating, 5 stars2 weeks ago

Great older lake house vibe. We liked it very much. It worked great for our family of five.

4.93 out of 5 average rating, 90 reviews

A wooden observation deck is surrounded by tall trees, providing views of a calm waterway reflecting the soft colors of the sky. The scene conveys a sense of tranquility, enhanced by the natural surroundings and the serene water's edge.

Guest suite in Duxbury

Guest suite on cranberry bog, 1 mile from beach

MelissaRating, 5 stars1 week ago

Lovely property in a wonderful area. Amazing hosts. Perfect, peaceful getaway. Helpful guestbook for everything we needed to know about their lovely home and Duxbury/Plymouth. Loved walking the dog around the beautiful cranberry bog.

4.95 out of 5 average rating, 21 reviews

A bright bedroom features a spacious bed dressed in crisp white linens. Three windows offer panoramic views of the water, allowing natural light to fill the space. A white shelving unit stands to the side, enhancing the room's functionality.

Home in Hull

Every room a water view updated kitchen & bath

JohnRating, 5 stars3 months ago

Excellent experience. Easy check in and the place was perfect, she even had some snacks waiting for us upon arrival. Easy walk to the ferry into Boston, and easy parking. It was winter, but there were plenty of outdoor activities so we'd love to come back during the summer. Older house but so charming and great location. Overall great communication before, during, and after; she even offered to ship a shoe my niece left behind to us. Would love to come back and would absolutely recommend to anyone looking for a great place in Hull.

4.84 out of 5 average rating, 31 reviews

Apartment in Brighton

The Curie-Perfect for Monthly Stays

XuemeiRating, 5 stars1 week ago

This apartment is a great find! The location is perfect, not far from Boston, near every colleges for those who come visiting! This apartment building is indeed very new, built in 2021; but also blended in with history, the leasing office/lobby was converted from an old day chapel, pristine, elegant. Very unique Airbnb experience indeed. The small town is full of vibe with various kinds of cuisines, very good for families, young or old. Melissa, the host is super, giving us very detailed information and instructions from parking to checking in, every tiny details she thoughtfully considered. We couldn’t be happier to stay in this apartment. Highly recommended!

4.99 out of 5 average rating, 165 reviews

A sunlit front porch is revealed, featuring comfortable seating arrangements with soft, textured cushions. A wooden coffee table sits in the center, accompanied by decorative elements such as candles. Large windows allow natural light to flood the space, complemented by greenery in potted plants.

Cottage in Newburyport

True North Cottage*Ocean side of Boat Basin!*

ErikRating, 5 stars6 months ago

Located just a short walk to the beach this charming cottage offered the perfect blend of comfort and convenience for my whole family. The spacious cottage was clean and very well designed with everything we needed for a relaxing stay, including a fully equipped kitchen and cozy living area with modern amenities. The hosts, Elia and Rob, were incredibly welcoming and accommodating and we hope to visit again soon. I would highly recommend True North Cottage to anyone looking for a peaceful getaway near the beach and scenic, downtown Newburyport.

4.91 out of 5 average rating, 122 reviews

An outdoor covered porch is depicted with a round dining table surrounded by four chairs. A gas grill is positioned near a seating area that includes a couch and two lounge chairs. The home's wooden shingles provide a natural backdrop.

Home in Gloucester

Gloucester Beach House, near Good Harbor Beach!

TashaRating, 5 stars3 months ago

Our stay at the Gloucester Beach House was great. It is a nice walk down to Good Harbor Beach, The Common Place Market and the neighborhood is peaceful. Its about a 10-minute drive to anywhere you want to go in Gloucester. Diane was responsive with any communication we had with her, and stayed in contact with us throughout the trip. We were grateful to be able to check in early after traveling all night to rest before beginning our trip adventures. For anyone interested, the Rhumb Line currently offers live music every night and its a variety of music. We went there several times and the musician's were top notch, and this is a place where the locals gather. We ended up visiting with friends and family and looking forward to another trip out to explore more of North Shore! Thank you so much for the wonderful home and stay.