Waterfront vacation rentals in Gloucester

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Top-rated waterfront rentals in Gloucester

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Eliot

4.98 out of 5 average rating, 122 reviews

Salty Mermaid Cottage/Boat House

This 2br home is nestled at the end of a peninsula’s over the water, 5min drive to downtown Portsmouth. Spend the day on the on deck, grilling or enjoy your own authentic Maine lobster bake, swimming and treasure hunting the shore. Also explore Kittery or downtown Portsmouth, both just five minutes away. Enjoy this freshly renovated home, water views from every room and window, all bedrooms are equipped with a/c, free WiFi and smart TVs. Fully equipped kitchen has an amazing view of the water.

Guest favorite

Rental unit in Arlington

4.98 out of 5 average rating, 184 reviews

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.

Guest favorite

Home in Sandown

4.95 out of 5 average rating, 19 reviews

Private Waterfront home

WATERFRONT HOME! Come escape to this home on the lake. Get ready to kyak, waterski, swim, fish or just relax on the large new deck & watch the sunsets. This Crate & Barrel-esque styled Cape has room to entertain & sleep plenty of guests. Sit, relax & listen to the loons. Sonos speaker system throughout the home and outside. 2 kyaks & a pedal boat for guest use. Boat launch is next door. Hannaford Grocery store & Walgreens is 1 mile away. Enjoy the Fire pit & fire up the grill.

Guest favorite

Condo in Rockport

4.96 out of 5 average rating, 76 reviews

Rockport Oceanfront: Take the Train to Salem

Dreaming of a magical seaside getaway? Our charming eco-apartment in the Dream House awaits you! A beach lover's paradise, we're located directly on the ocean in the heart of downtown on Bearskin Neck. Watch the sunset from our amazing windows overlooking the harbor. Steps to shopping, dining, art galleries, Front Beach and Motif #1. A short drive to Halibut Point for wonderful walks and an easy train ride or drive to Salem. Make a trip to this delightful seaside village a priority!

Guest favorite

Home in Portsmouth

4.88 out of 5 average rating, 213 reviews

Charming Riverfront Cottage in Portsmouth-SouthEnd

This super comfortable, newly renovated (Nov 2022) and charming little cottage on the river couldn't be more convenient to all that the city and surrounding area has to offer. Enjoy true walking access yet be in a quiet 18th century neighorhood. Across the street from the historic Portsmouth waterfront and around the corner from Pierce Island, Prescott Park, Strawbery Banke and Point of Graves, 112 Mechanic is an incredibly charming home. No pets please. Street park with ease.

Guest favorite

Home in Kittery Point

5 out of 5 average rating, 102 reviews

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

Guest favorite

Home in Kittery

4.95 out of 5 average rating, 134 reviews

Gorgeous Waterfront Home with Dock and Beach

Looking for a wonderful location to enjoy a week this summer in Maine? We have a beautiful location right on the water for you and your family to enjoy. HAVE A BOAT and want to bring it with you? We have a deep water dock. Ask us about details and cost. House is on a dead end road. Come & enjoy the Maine coast! We are located 2 miles from Portsmouth, and there are numerous activities to do in this area. Golfing, Boating, Swimming, Outlet shopping and of course the Beach!

Guest favorite

Home in Gloucester

4.98 out of 5 average rating, 46 reviews

Swim in Summer, Ski in Winter—Waterfront Sunsets!

Stunning sunsets, a parade of boats going by, a charming marina and a beach brimming with natural beauty—these are the sights you’ll behold at this year-round waterfront home built to maximize its spectacular maritime views. The modern yet cozy house features a balcony overlooking the water. An open floor plan allows for maximum water views from the kitchen, dining and living areas thanks to an expanse of windows across the entire first floor. Registration #: C0176131070

Guest favorite

Cottage in Portsmouth

4.89 out of 5 average rating, 38 reviews

Portsmouth Waterfront Cottage

Our waterfront cottage is a unique property offering style, tranquility, and walking access to Portsmouth’s Market Square. The theme is a blend of New England charm and Scandinavian modern. We offer an amazing view, two decks, a modern kitchen, laundry, and free parking for one vehicle. This premium property sleeps three, counting children. It offers a quiet romantic escape for the discerning traveler, and yet is just a ten minute walk to Market Square.

Guest favorite

Cottage in Kittery Point

4.98 out of 5 average rating, 42 reviews

*Discount* Waterfront Cottage on Chauncey Creek

Charming Cottage Rental on Chauncey Creek! Cottage features 2 bedrooms and 1.5 baths. This 1.3 acre property has over 300 feet of beautiful water frontage and a private dock on the famous Chauncey creek. Bring your boat/ canoe/ kayak and enjoy all the wonderful pluses of this waterfront location. This charming waterfront cottage is only 4 miles outside all the shops, restaurants, breweries, and entertainment offered by beautiful downtown Portsmouth, NH!

Guest favorite

Guest suite in Hull

4.96 out of 5 average rating, 25 reviews

Sunset Point Waterfront Apartment

Best location in Hull! Remodeled studio on Sunset Point with direct views of Worlds End and Hingham Bay. Private parking for your car and private mooring for your boat with shared dock, canoe and grill. Fully equipped kitchen with all new appliances, spacious living room with biofuel fireplace, modern bath including washer & dryer, private patio for lounging or dining al fresco as you watch the ever-changing and always spectacular sky and water views.

Guest favorite

Cottage in Newburyport

4.92 out of 5 average rating, 104 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.