
Beachfront holiday rental in Wingaersheek Beach
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Top-rated beachfront accommodation in Wingaersheek Beach
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Actual Filming site of Widows Bay! Harborside Retr
Visit "Widows Bay", this was the cafe in the hit show. This apartment was featured in scenes of the hit show. Stay at this unbeatable location on scenic Bearskin neck. Step outside to beaches, art galleries, boutiques, and fresh seafood dining — all just moments away on foot. Perfect for couples or small families seeking a relaxing coastal escape. Historic charm blends with modern conveniences. A welcoming living space, and a full kitchen for easy meals after a day by the ocean. Private patio
4.9 out of 5 average rating, 209 reviews
Downtown Waterfront Escape: Views, Parking & Deck!
Stunning water views meet historic charm! Enjoy this renovated waterfront apartment in a historic downtown home with separate entrance and your own deck. Enjoy a cup of coffee or glass of wine in the backyard adirondak chairs facing the water. Rare onsite parking makes everything easier. Just steps from beaches, dining, live music, and Bearskin Neck shopping. Features a full kitchen with new appliances, Keurig, Roku TV, games, and a cozy living area. Your perfect, walkable Rockport getaway.
4.99 out of 5 average rating, 287 reviews
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).
4.96 out of 5 average rating, 152 reviews
*Beachfront* Vintage Coastal Cottage - Relaxation
It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here once you book I can send you a link (per Airbnb’s rules) I’ve outfitted it with an extra monitor & a setup o WFH. Google home and Sonos systems bring this 100 year old beauty into this century.
4.98 out of 5 average rating, 388 reviews
Mary's By The Sea
A unique 650 square foot ground floor apt across the street from Front Beach. 6 minute walk from the Rockport MBTA . There is a separate bedroom with a queen mattress and a pullout sofa bed in the living area. The pullout sofa is best for teens or smaller kids . There is a bathroom with a sink and toilet. There is another room with a sink and shower. The kitchen area is more like a kitchenette than a full-size kitchen. We provide one parking spot next door at The Cove parking lot.
4.95 out of 5 average rating, 234 reviews
Seadrift Inn - 2 bedroom 2nd floor apt by the sea!
We are at Salem Willows - family-friendly activities, the ferry, trolley, train, downtown, and nightlife are all close by. Seadrift is perfect for couples traveling together as it has two bedrooms, both with King beds, a large living room, and bathroom. You have a private entrance and it is located on the second floor. You can walk to four beaches within minutes, one is right outside your door. Salem has many historic landmarks and wonderful restaurants very close by. Come visit!!
4.96 out of 5 average rating, 289 reviews
Rocky Neck Studio/Loft, Gloucester, Mass.
Welcome 2026! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV
4.92 out of 5 average rating, 257 reviews
Harbor Place - Airy hideaway over Rockport Harbor
Enjoy stunning views of Rockport Harbor and the Atlantic from Harbor Place, a breezy, quiet open-floorplan bnb on Tuna Wharf, steps from the galleries, shops and restaurants of bustling Bearskin Neck. You'll be within easy strolling distance of several beaches, the train station, the Shalin Liu Performance Center, kayak rentals, walking paths, parks and boat tours. Relax and enjoy the view, eat in or out, lounge on our private beach! Access to Harbor Place is via staircase.
4.99 out of 5 average rating, 139 reviews
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.
4.91 out of 5 average rating, 319 reviews
Ocean Wave unit, Melo's Beach House Rentals
Monthly rates available for winter months. PM if interested. Salisbury Beach! Adorable 2 bedroom beach house apt. on Salisbury Beach. Kitchen, living room and 1 full bath. Full size deck with sliders. Cozy and clean. Approx. 480 feet from the beach. A short walk to Salisbury center, for pizza, fried dough, ice cream, arcades and some night life. We supply bed linens, pillows, towels and much more. (listing is 1 of 3 units on property) no pets and no smoking in units.
4.86 out of 5 average rating, 132 reviews
Spacious waterfront, free parking &Wi-fi
Amazing beach and ocean front -Full kitchen -2 bedrooms,Spacious living area -1 bathroom -Laundry room -Parking for 2 cars -Towels and linens -Air-condition/heat -Smart TV & free WiFi -Blackout curtains in bedrooms -Condo Sleeps up to 8 people -Room 1 has king bed sleep 2 -Room 2 has 2 full beds sleeps 4 -Living area has 2 couches -Lyft chair for stairs to go up and down “you must request to use and get the key” Beach is across one way street.
4.9 out of 5 average rating, 264 reviews
Spectacular Views of Rockport Harbor.
The Mooring Stone Guest House is located directly on Rockport Harbor across from Motif #1 & Bearskin Neck. Enjoy your harbor-facing suite with private bath & patio. Private entrance affords you freedom to come & go at will. Fabulous, interesting & ever-changing views make for great photo opportunities & will keep you entertained in this quaint New England seaside village. Self- Check-In (how to info given near to occupancy date).
4.94 out of 5 average rating, 168 reviewsPopular amenities for Wingaersheek Beach beachfront rentals
Pet-friendly beachfront home rentals

Oceanfront Retreat | Salem 7 min by train
4.93 out of 5 average rating, 144 reviews
Oceanfront Oasis:Stunning &Spacious 1st Fl 1BR #1
4.88 out of 5 average rating, 136 reviews
Truly Oceanfront! Spacious Family Petfriendly Home
4.99 out of 5 average rating, 242 reviews
Beach Home next to Boston & T, King Bed, Park Free
4.93 out of 5 average rating, 201 reviews
Lakeside apartment, patio, hot tub, outside shower
4.98 out of 5 average rating, 221 reviews
City Sanctuary Private Terrace and Ocean Views
4.87 out of 5 average rating, 116 reviews
Chic Gloucester Escape•Harbor&Dining•Close2Salem
4.93 out of 5 average rating, 30 reviews
Blue Wave North
4.97 out of 5 average rating, 63 reviewsBeachfront home rentals with a pool

Sunset Waterfront Retreat | Private Beach, Pool &
4.93 out of 5 average rating, 141 reviews
Oceanfront Pool. Close to Boston. Free Parking.
4.96 out of 5 average rating, 285 reviews
406 Co. Seascape
4.97 out of 5 average rating, 102 reviews
Whale's Tale - Boutique Studio Condo with Pool
4.95 out of 5 average rating, 61 reviews
Ocean View - Steps to the Beach!
4.96 out of 5 average rating, 55 reviews
Surfside - Boutique Studio Condo w/Pool
4.92 out of 5 average rating, 59 reviews
~Salty Sunsets & Sandy Toes~ 493 Ocean Blvd
5.0 out of 5 average rating, 4 reviews
Relaxing oceanfront North Beach condo with a pool!
4.75 out of 5 average rating, 28 reviewsPrivate beachfront home rentals

Welcome to the Beach Escape! Seabrook, NH
4.81 out of 5 average rating, 202 reviews
The Wave • Ocean condo on sands of Hampton Beach •
4.94 out of 5 average rating, 131 reviews
Adorable beach cottage with kitchen
4.94 out of 5 average rating, 115 reviews
Oceanfront, private balcony, panoramic ocean views
4.91 out of 5 average rating, 107 reviews
Oceanview Condo
4.9 out of 5 average rating, 142 reviews
Surfer's Sunrise Studio Beach & Fireworks View
4.89 out of 5 average rating, 118 reviews
Front Beach House Getaway! Fall specials!
4.9 out of 5 average rating, 51 reviews
Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets
5.0 out of 5 average rating, 25 reviewsDestinations to explore
- Fenway Park
- Ogunquit Beach
- Hampton Beach
- Harvard University
- Wells Beach
- TD Garden
- Boston Seaport
- Gillette Stadium
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Long Sands Beach
- Freedom Trail
- Short Sands Beach
- New England Aquarium
- Boston College
- Northeastern University
- Canobie Lake Park
- York Harbor Beach
- Duxbury Beach
- North Hampton Beach
- MIT Museum
- Cape Neddick Beach





