Vacation rentals in Winthrop

4.92 out of 5 average rating, 1,300 reviews

The entrance features a white door framed by beige siding, providing accessibility with a welcoming vibe. A sign indicates its Airbnb status. A terracotta pot filled with vibrant yellow and purple pansies adds a touch of natural beauty next to the entrance, enhancing the inviting exterior.

Guest suite in Winthrop

Licensed Boston airport studio 5 stars, subway

We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

4.91 out of 5 average rating, 286 reviews

A compact kitchen is equipped with white cabinetry and a stainless steel stove. Natural light enters through a window, illuminating the counter. A dining table is set with blue and white dishware, creating a simple and functional cooking space. A doorway leads to the adjoining living area.

Apartment in Beachmont

Boston 3 Room Apt 5 Min Walk to Train & Beach

Listing description Sunny 3 room apartment with private entrance. Just 1 block from the ocean and short walk to Revere Beach. The MBTA Blue Line is a short 10 minute walk, be at Logan Airport or Downtown Boston in minutes. The apartment has a full kitchen, spacious master bedroom with king size bed and TV. The living room has a TV, sofa, comfortable twin size day bed with a privacy door between B.R. and L.R. Visit historic Salem via public transportation. Laundry on site. Free Driveway Parking.

The outdoor area features a serene saltwater pool surrounded by lounge chairs, all set against a backdrop of panoramic ocean views. A pergola provides partial shade, and vibrant flowers add a touch of color to the landscaped surroundings.

4.96 out of 5 average rating, 241 reviews

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

4.94 out of 5 average rating, 129 reviews

Apartment in Nahant

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

4.99 out of 5 average rating, 186 reviews

Condo in Winthrop

Truly Ocean-Front!: Spacious Family Home + Pets

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

4.99 out of 5 average rating, 123 reviews

The modern kitchen features a large island with granite countertops, offering a functional space for meal preparation. Sliding glass doors provide unobstructed ocean views and access to the outdoor deck. A cozy gas fireplace is visible in the background, enhancing the inviting ambiance.

Apartment in Beachmont

Beachmont Guest Suite

Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

4.98 out of 5 average rating, 466 reviews

A sandy beach stretches along the shoreline, gently illuminated by a vibrant sunset. A staircase leads down to the beach, hinting at accessibility. In the distance, the silhouette of a water tower marks the community, while the sun sets over the calm ocean waves.

Cottage in Winthrop

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

Superhost

An air mattress is displayed within its packaging. The blue top surface is smooth with raised sections for comfort. Icons on the front indicate features like inflation and deflation functions. The product is positioned against a light background, highlighting the mattress design.

4.74 out of 5 average rating, 175 reviews

Heavenly Hideaway Boston Airport Beach Park Free

Private spacious 1 bedroom 1 bath attic apartment with new rug/paint/ac. Nice little skyline view of Boston in a beautiful safe quiet residential neighborhood. Great place to rest your head or use as a base to Boston The Encore Casino Salem & beyond! Bedroom comfy mattress/sheets 55” Smart TV blackout shade ceiling fan nightstands lamps 2 chairs Living Areas sofa bed 55” Smart TV sitting chair table 2 chairs/lamps Kitchenette fridge microwave Keurig toaster oven dishes silverware glass

4.98 out of 5 average rating, 102 reviews

A welcoming porch area is featured, with a round dining table under a large umbrella, surrounded by colorful planters. Two rocking chairs are positioned nearby, while soft lighting adds warmth to the inviting space.

Guesthouse in Melrose

Jimmy & Donny's AirBnB

Beautiful, 2 level guesthouse! Private entrance, bedroom/bath/living area. NOTE: BEDROOM/BATHROOM ON SECOND FLOOR UP SPIRAL STAIRCASE. Large porch. Melrose is located 7.5 miles north of Boston, 2 convenient train stops, 20 minutes away, into downtown Boston. A short walk to The Fells Reservation, hiking & kayaking, or visit the Stone Zoo. We have Italian/Seafood/Mexican/Spanish/Mediterranean & Revolutionary Style Tavern restaurants in Melrose. Owners always on property. NO PETS/NO KIDS.

4.95 out of 5 average rating, 933 reviews

A wooden pier extends into calm waters, flanked by metal railings. Lanterns stand at intervals along the walkway, which leads toward the horizon. Soft clouds are visible above, with a mellow sun illuminating the scene.

Guest suite in Winthrop

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

4.94 out of 5 average rating, 152 reviews

Apartment in Woburn

Your Cozy 1 BR Apt & Relaxing Retreat

Welcome to your romantic 1-bedroom apartment in Woburn, the ultimate escape for couples looking for relaxation and charm. Enjoy a private jacuzzi 🛁 and a cozy fire pit 🔥—ideal for creating unforgettable memories. Step right out from the bedroom to the jacuzzi and outdoor space, allowing you to unwind in the soothing waters while enjoying the warm ambiance of the fire pit. Perfect for a romantic retreat, this intimate space provides everything you need for a truly enchanting stay.

Superhost

A decorative lamp features a cylindrical base filled with an assortment of seashells, showcasing a variety of shapes and sizes. The lamp is topped with a white shade, creating a cohesive coastal-inspired design. A decorative flower vase in light blue adds a complementary touch.

Guest suite in Winthrop

4.86 out of 5 average rating, 118 reviews

The Strand on the Beach

Welcome to the 129 The Strand! This accommodation will transport you to a tropical paradise where you can relax and enjoy the sun, sand and sea. Located a few steps from the beach, our Airbnb is the perfect place for your dream vacation. The interior is decorated in a modern and cozy style, and is equipped with everything you need for a comfortable and relaxed stay, it has 1 bed, 1 bath, living room, private entrance, parking, & refrigerator.

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Popular amenities for Winthrop vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Winthrop

The exterior of the apartment building features grey shingles and a paved area. A white door with a decorative window leads inside. A balcony with a white railing is visible above, providing additional outdoor space. The area appears well-maintained with ample natural light.

4.89 out of 5 average rating, 76 reviews

Vibrant Winthrop Apartment - Close to Ocean!

4.97 out of 5 average rating, 62 reviews

Pleasant Place 2

4.89 out of 5 average rating, 19 reviews

A panoramic view of the calm Atlantic Ocean is captured, showing gentle waves lapping at the shoreline. A soft gradient of colors in the sky transitions from blue to warm hues, reflecting the tranquility of the evening atmosphere.

Cottage in Beachmont

Ocean Front cottage flat 30 day minimum

4.88 out of 5 average rating, 48 reviews

Skyline view spacious 3bd close Boston/beach/Airpt

4.87 out of 5 average rating, 68 reviews

Home in Winthrop

Cozy & Modern Entire Residential Home ❤️

A front porch is seen with wooden flooring and white siding, featuring a comfortable chair and various potted plants. Natural light illuminates the space, and a glimpse of the street and nearby houses can be observed in the background.

4.85 out of 5 average rating, 20 reviews

Charming condo steps from beach

4.99 out of 5 average rating, 68 reviews

A private roof deck is showcased with a round table and four high-backed chairs beneath a vibrant red umbrella. Wooden decking and a slatted privacy screen provide an inviting outdoor space, complemented by a small potted plant in the corner.

Condo in Winthrop

The Day-Burrill-Wadsworth-La Voix House