
Waterfront holiday rentals in Winthrop
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Winthrop
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

Luxury Oceanview Suite in Victorian on Independence Park
Bask in beautiful sunrises and peaceful ocean sounds from a generous seaside room with wet bar. The 42” Art Frame TV offers Xfinity, Netflix, and Hulu Plus apps, while the space itself has large windows and a bright, sophisticated interior and is only steps from the beach. Terrific ocean views from this newly renovated suite. Easy access to the beach, paddle board rentals on the weekend right outside your door, walking to Dane Beach, a quick walk to Cabot Street and the cafe's and restaurants nearby. A well equipped wet-bar with fridge, freezer, microwave, coffee maker and tea set ups, and a newly renovated bathroom with heated floors and double shower complete the space. A 42” Art Frame TV with the Xfinity, Netflix and Hulu Plus apps. Enjoy your favorite shows or leave the TV in art mode. We are available by phone or text always but we live just a few houses away, so we can be reached almost anytime. We generally leave guests alone and respect your privacy but can be available if necessary. On the North Shore of Massachusetts, about 26 miles from Boston, Beverly has small-town charm coupled with a city identity. Located close to vibrant Cabot Street in downtown, there are recreation, shopping, and dining options for all tastes. Beverly has excellent access to Route 128 and five commuter rail stations. The house is just a 10-15 minute walk to the Beverly Depot (first Beverly stop on the MBTA commuter rail). It's a bout a 20 minute ride to North Station in Boston.

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.

Lakeside apartment, patio, hot tub, outside shower
Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

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.

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.

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!

Ocean Views at Casa de Mar near Salem & Boston
Relax and unwind at Casa de Mar - our 3 bed, 3 full bath ocean front home on the North Shore. Close to Salem and Boston, overlooking Swampscott Bay to Nahant. The great room has 25' ceilings, a 70" flat screen TV, and 2 seating areas. Modern kitchen, new appliances. The master bedroom has a king-sized bed, sitting area, flat screen TV, private balcony, and en suite bath. The first floor bedroom has a queen bed and a private balcony. The third bedroom has a queen bed and en suite bath.

Sunset LAKE VIEW studio. Recently upgraded!
Welcome to Sunset Lake! Enjoy beautiful sunsets year round! Cozy in the winter with plenty of extra blankets and a great heating system! Light a fire at night. We are walking distance to South Braintree Square. You will enjoy nature and still have close proximity to city. Walk to a super market, pharmacy, nail salon, bank, a tavern w/ live music. Other restaurants within walking distance include Mexican, Thai, Sushi, Italian, Vietnamese (pho), pizza and a great local coffee shop ☀️ 🌅

Rock Steady - Panoramic Ocean Front Home
Just north of Boston, our home is a mid century ranch we renovated in 2019. The Airbnb is a spacious ground floor living space surrounded by a private cove that is truly breathtaking. 1000 square feet of sunlit comfort. Enjoy the sound of the waves, stunning sunrises and a landscaped back patio that abuts our cliff. In the summer take advantage of the town beach down the street. During the winter relax in front the fireplace. Top it all off with hi-speed Wi-fi – it's a perfect getaway.

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.

Ocean Park Retreat
Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Enjoy Stunning Sunrises&Sunsets Ocean Views 33
This Airbnb offers a relaxing atmosphere with serene surroundings. It is situated directly across from the ocean and diagonally across from Dane's Beach and Playground. The 719 sq feet if loving suave consist of . It includes Wi-Fi, a newly furnished, recently updated, fully equipped kitchen, 3 smart TVs, master bedroom and another room with two double beds. The Airbnb is just a few minutes away from downtown Beverly and only a 10-minute drive to Salem
Popular amenities for waterfront rentals in Winthrop
Waterfront apartment rentals

2bed/2bath Apt at Waltham Landing. Middle Unit

Winter Island Retreat

Spacious 2B Entire Home near Boston, Salem& Encore

Mariam’s On Becket

House of Three Gables

Modern Coastal City Stay | Waterfront & Airport

Ocean front spacious condo

Seaside Getaway - Ocean Views
Waterfront house rentals

WATERFRONT-15 min to BOS/3BdRm/2BA

Marblehead Neck Cottage, Harbor Views & Roof Deck

4 bd Ocean View, Dual Deck, Beach Front Retreat

Entire Historic Home Overlooking Maritime Park

The Sunset Lighthouse Marblehead

River Retreat - Close to Boston

Boston by the Beach — Steps to T Station

*NEW Spooky Halloween |2BR|Downtown Salem|Parking
Waterfront apartment rentals

Newly renovated Boston Condo

Salem Sanctuary by the Sea

Eastie near the airport Great location

Stunning Waterfront Condo with Boston Skyline View

Modern Seaside Penthouse Condo (Historic Salem)

Cozy Coastal Condo: Steps to Downtown & Waterfront

Luxury Sand Castle Beach House Historic SALEM

Boston Harbor View!Free Parking!North End 3 bed
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $231 SGD | $237 SGD | $239 SGD | $276 SGD | $292 SGD | $298 SGD | $321 SGD | $321 SGD | $321 SGD | $319 SGD | $293 SGD | $231 SGD |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Quick stats about waterfront rentals in Winthrop

Total holiday rentals
Explore 20 holiday rentals in Winthrop

Nightly prices starting at
Winthrop holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 2,910 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Winthrop holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winthrop rentals

4.9 Average rating
Winthrop stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
Winthrop’s top spots include Orient Heights Station, Beachmont Station and Suffolk Downs Station
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Rentals with outdoor seating Winthrop
- Pet-friendly rentals Winthrop
- Rentals with a patio Winthrop
- Beachfront rentals Winthrop
- Rentals with a washing machine and dryer Winthrop
- Rentals with a fireplace Winthrop
- Fitness-friendly rentals Winthrop
- Family-friendly rentals Winthrop
- Rentals with beach access Winthrop
- Flat rentals Winthrop
- House rentals Winthrop
- Waterfront rentals Suffolk County
- Waterfront rentals Massachusetts
- Waterfront rentals United States
- Hampton Beach
- TD Garden
- Fenway Park
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- New England Aquarium
- MIT Museum
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Massachusetts Institute of Technology
- Museum of Fine Arts
- Quincy Market
- Onset Beach
- Prudential Center
- North Hampton Beach
- Roger Williams Park Zoo
- Boston Children's Museum
- Roxbury Crossing Station
- Salem Willows Park
- Franklin Park Zoo




