Vacation rentals in Winthrop

4.83 out of 5 average rating, 150 reviews

A spacious outdoor deck is furnished with black rattan chairs, providing comfortable seating for gatherings. The ocean view stretches out across the horizon, with boats visible on the water. The inviting atmosphere is complemented by clear skies and distant coastal scenery.

Bungalow in Beachmont

Cape cod style seaside condo Boston, Airport,Train

The Pier House, Cape Cod style beachside cottage near Boston, Fenway Park, and Boston’s finest restaurants and entertainment. 10 minutes walk to the train, 10-15 minutes to the airport &Boston. The Pier House is a condo with 1 master bedroom & 2 attach bedrooms walk-through,& 2full baths,2 ocean view balconies, Fireplaces,Beach access &water purified throughout the units. Just Renovated 2picture windows, updated kitchen. One car parking 600ft to private spot. No early check-in or late check out.

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.

4.97 out of 5 average rating, 333 reviews

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.

4.92 out of 5 average rating, 1,358 reviews

A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.

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.

A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.

4.96 out of 5 average rating, 265 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.

4.92 out of 5 average rating, 243 reviews

A light-filled corner of the living area features a sectional sofa in soft gray, complemented by a small coffee table. Three windows dressed in blinds allow natural light to filter in, enhancing the cozy and inviting atmosphere.

Apartment in Beachmont

Quiet Neighborhood Luxury Stay

The apartment is brand new with a modern feel to it. Available with all the amenities needed for your convenience. Very quiet, clean, and safe neighborhood. Close to everything you desire, 1 minute to the beach, 8 minutes away from the train station, 1 minute away from the T-Bus stop, 9 minutes to Logan Airport, 12 minutes to Downtown Boston, 15 minutes away from Encore Casino, food and coffee shops, such as Starbucks and Dunkin' Donuts in the area. Perfect for a family stay or a business trip.

4.94 out of 5 average rating, 158 reviews

A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.

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, 216 reviews

Condo in Winthrop

Truly Oceanfront! Spacious Family Petfriendly Home

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.

4.98 out of 5 average rating, 485 reviews

The exterior of the private studio is shown, featuring a light blue siding with a gray shingled roof. A welcoming front door is flanked by a light fixture and a decorative sign. Flowering plants are arranged in front, enhancing the outdoor space.

Cottage in Point Shirley

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.

4.89 out of 5 average rating, 231 reviews

The spacious living room features hardwood floors with an orange accent wall and contemporary artwork. A comfortable sofa and decorative throw blankets are arranged around a coffee table adorned with seasonal decor. A faux fireplace adds a decorative touch, while a small bench provides additional seating.

Apartment in Beachmont

Stunning Oceanview-4 Train Stop Logan Airport

Stunning 1 bedroom huge apartment with partial ocean views of Revere Beach. This upscale home has it all!! Just one flight up then you enter a hardwood floor foyer, opens to a huge living room with upscale decor, large eat in kitchen stainless steel appliance, country table has seating for 4, tile floor, gas range, and lots of cabinet space, with views of Revere Beach and ocean, giant bathroom complete with tiled shower and stackable laundry (Washer and Dryer) and huge bedroom with closet.

4.86 out of 5 average rating, 104 reviews

A well-lit dining area features a wooden table surrounded by chairs, complemented by a decorative chandelier overhead. The open layout allows for a view into the comfortable living area, where soft seating and natural light create a relaxed ambiance.

Home in Winthrop

Sunny 3 bedroom on beach

Welcome to our beautiful 3 bedroom apartment on the beach! Enjoy stunning ocean views and easy access to Winthrop Beach, only 2 minutes away. Accommodations for up to six guests, making it perfect for families or groups of friends. Bright and airy living area with plenty of natural light and a cozy seating area, perfect for relaxing after a long day at the beach. The dining area offers ample seating, and the fully equipped kitchen, private deck with breathtaking views of the ocean.

Guest suite in Point Shirley

An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.

4.94 out of 5 average rating, 1,005 reviews

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with 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.

4.95 out of 5 average rating, 125 reviews

The living room features two sofas, one in a solid color and the other with a striped pattern, facing a large window that offers ocean views. A light-colored area rug lies on the wooden floor, and a simple coffee table is centered in the space.

Apartment in Beachmont

2 Bedroom Apartment with Ocean Views

Quiet, newly renovated 2 bedroom apartment just outside Boston 180 degree ocean views 10-15 min walk to subway with quick access to Goverment Center, MGH, Aquarium, North End and TD Garden. Beach access accross the street and short walk to Revere Beach. Lots of good resturaunts and cafes nearby. Unit is located on the 3rd floor. 3 sets of stairs to access apartment. Perfectly safe but not handicap accessible or convenient for anyone with impaired mobility or small children.

Popular amenities for Winthrop vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Winthrop

Superhost

A spacious bedroom features large windows that provide panoramic ocean views. A comfortable bed is centered in the room, complemented by a soft throw pillow. Elegant light fixtures hang from the ceiling, and a cozy armchair sits beside the windows, enhancing the serene atmosphere.

4.85 out of 5 average rating, 52 reviews

Oceanfront Penthouse Retreat

The exterior of a stylish two-family home is depicted, featuring a welcoming porch with white railings and a neatly landscaped front yard. Flowering plants, small trees, and a paved pathway lead to the entrance. The upper floor includes strategically placed windows, allowing natural light to filter in.

4.98 out of 5 average rating, 93 reviews

Pleasant Place 2

4.93 out of 5 average rating, 382 reviews

A charming outdoor seating area is framed by a white fence and vibrant greenery. Comfortable seating is arranged around a low table, with bright orange cushions adding a lively touch. Potted plants with colorful flowers complement the inviting space, creating a pleasant atmosphere.

Home in Everett

Prime location near Boston

4.89 out of 5 average rating, 80 reviews

A well-furnished living area features a light-colored sofa adorned with patterned cushions, complemented by a blue ottoman. A large area rug in soft tones enhances the warmth of the hardwood floor. Natural light enters through multiple windows, while a decorative chandelier hangs from the ceiling.

Home in Winthrop

Cozy & Modern Entire Residential Home ❤️

4.98 out of 5 average rating, 100 reviews

The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.

Condo in Winthrop

The Day-Burrill-Wadsworth-La Voix House

4.83 out of 5 average rating, 47 reviews

A spacious living room features two comfortable sofas adorned with bright floral cushions, complemented by a light throw blanket. A wooden coffee table sits centrally, and large windows allow natural light to fill the area. Decorative accents include a wall clock and a floral vase.

Home in Winthrop

3 bdr, steps from the ocean, minutes from Boston

4.97 out of 5 average rating, 109 reviews

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

The sweet suite

A private wooden deck with seating arrangements offers expansive views of sandy Winthrop Beach and the ocean. The tranquil shoreline is visible, with gentle waves lapping against the shore, while the clear blue sky stretches above, creating a serene coastal atmosphere.