Holiday houses in Wingaersheek Beach

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Top-rated holiday rentals in Wingaersheek Beach

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Guest favourite

Rental unit in Rockport

4.96 out of 5 average rating, 114 reviews

Harborside Oasis | Harbor View | Heart of Downtown

Step into Coastal Bliss at Our Rockport Apartment! 🌊🏠 Perfectly positioned just steps from Bearskin Neck, immerse yourself in unique shops 🛍️, exquisite dining 🍽️, and serene beaches 🏖️. Revel in the spectacular views of iconic Motif Number 1 from your balcony, enjoy high-speed WiFi, and a 55" Smart TV in a fully stocked kitchen. Ideal for soaking in Rockport's vibrant yet relaxing atmosphere. Note: Requires climbing stairs and can get noisy! Book your unforgettable seaside retreat today! ⚓

Guest favourite

Home in Gloucester

4.95 out of 5 average rating, 133 reviews

Views over Lobster Cove!

Booking summer and fall 2024. Water views/access, sunsets above Lobster Cove on Washington St. Ideal for couple, NEW KING BED in master, queen in 2nd. Fast WiFi./TV. Not suitable for young children. Central A/C. 2nd fl unit large windows. Large living/dining/kitchen area. Comfy new mattresses, 100% cotton sheets,sound machines. Overlooks beautiful Lobster Cove and footbridge. Minutes walk to the village of Annisquam and Lighthouse Beach. Small deck. Swim/kayak out your door. Parking for one car

Guest favourite

Condo in Rockport

4.98 out of 5 average rating, 182 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

JUST OPENED NOV/DEC DATES! From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream/coffee, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport on Bearskin Neck. Enjoy beautiful ocean breezes with coffee or cocktails on the deck of this sweet beach retreat nestled on the N.E. coast. Come fall in love with charming Rockport!

Guest favourite

Guest suite in Gloucester

4.98 out of 5 average rating, 419 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2025 monthly rentals. Must Book Summer 2025 via Airbnb website not the APP! *Can't find an opening in SplashLanding? Our 2nd unit SquishInn has openings June-Oct 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples 2 friends can join you!

Guest favourite

Rental unit in Gloucester

4.94 out of 5 average rating, 127 reviews

Open Concept Eclectic Mod 3 BR

Salem is a quick drive away! Fall is here, come to Gloucester where you can get away from it all and still be close to everything! Give your family a cozy home base. You will be centrally located off Route 128 just minutes away from Good Harbor, Niles, Pavilion, Half Moon and Wingaersheek beaches, year round nature walks, downtown shops and restaurants, grocery stores, and the commuter rail to Boston. Enjoy a great base for exploring Cape Ann with drives to Essex, or Manchester by the Sea.

Guest favourite

Rental unit in Ipswich

4.88 out of 5 average rating, 269 reviews

Ipswich Apartment

The apartment, with a private entrance is located in downtown Ipswich. We are within walking distance to restaurants and the commuter rail, which services Salem, Boston etc. May - September, the CATA shuttle stops at the commuter rail station, a 3 minute walk. Some CATA services include Cranes Beach, and the town of Essex (famous for its clams and antique shops). You can also enjoy a river cruise down the Essex River there. Kayaking, canoeing, and fishing are also available in Ipswich.

Guest favourite

Cottage in Gloucester

4.97 out of 5 average rating, 124 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. In the off-season, a quiet escape -perfect for focused work, writing, painting or reading, Please contact host for discounts on longer stays (30 days + from Dec - April) Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

Guest favourite

Rental unit in Rockport

4.93 out of 5 average rating, 149 reviews

Hidden Gem! Short term rental steps from 2 beaches

Hidden Gem! Short term seaside rental. Lovely 1 bed 1 bath unit located on private wooded property, steps away from 2 beaches. Private unit amenities include wood burning fireplace & deck with gorgeous year round views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.

Guest favourite

Cabin in Rockport

4.97 out of 5 average rating, 431 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

Guest favourite

Guest suite in Rockport

4.98 out of 5 average rating, 661 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Guest favourite

Guest suite in Rockport

4.88 out of 5 average rating, 208 reviews

Charming Studio in the Pines

This is a first floor, above ground, garden apartment in a private home and is located in a quiet neighborhood with the backyard nestled in the woods, just out side your sliding door. Flower gardens and bird feeders adds ambiance for relaxing in a private setting. The studio offers a kitchenette, dining nook, a full bathroom, a queen bed, plus a sofa. Also available is CableTV, Netflix and Wi Fi.

Guest favourite

Guest suite in Manchester-by-the-Sea

4.92 out of 5 average rating, 146 reviews

Modern Space With Pool Close To Singing Beach

Situated in a very quiet neighborhood, you will rest comfortably. Drive five minutes and you can be in downtown Manchester-By-The-Sea with singing beach and great restaurants. secluded back yard with fire pit and pool. Inside you'll find a freshly updated and modern living space with fireplace. (Pool open from 5/27-9/8).