Waterfront holiday 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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Superhost

Holiday home in Natick

4.87 out of 5 average rating, 109 reviews

Private Lakefront with game room/Newly renovated

Ideal private location on crystal clear Lake Cochituate! Peaceful quiet spot w amazing view only 20 min to Boston & 1 or 2 min drive to anything u could need Fun game room &free use of tandem kayak & paddleboard and fishing Sliding barn door separates main king bedroom, bath, & open kitchen & livingroom from the back 2 queen beds, game room & bath Im always available to answer questions + provide tips, but I also respect your privacy & want u to feel comfy & independent 》25 6 person 3 car limit

Top guest favourite

Cottage in Eliot

4.99 out of 5 average rating, 142 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 favourite

Home in Manchester

4.97 out of 5 average rating, 38 reviews

Enchanting Romantic Riverfront (SNHU/Saint Anselm)

A riverfront oasis with 120' water frontage and private dock, this beloved guest favorite offers a dreamy escape full of tranquility and romance. The cottage exudes charm and elegance with its cozy interiors, adorned with rustic yet refined decor that blends seamlessly with the natural surroundings. Large windows provide stunning views, which are just above the water. Ideal for parents visiting: West Side Ice Arena: 5 minutes; Saint Anselm College: 8 mins; SNHU arena: 10 mins; Airport: 15 mins

Guest favourite

Flat in Arlington

4.98 out of 5 average rating, 193 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.

Superhost

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.

Top guest favourite

Apartment in Rockport

4.96 out of 5 average rating, 77 reviews

Rockport Oceanfront 1 Bed Apt Heart of Downtown

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 favourite

Home in Portsmouth

4.89 out of 5 average rating, 242 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.

Top guest favourite

Home in Gloucester

5 out of 5 average rating, 9 reviews

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

Waterfront Paradise! Sweeping ocean river views & gorgeous sunsets! Swim, paddle board or watch the tides come and go on the private dock and raft. Enjoy a book, nap or meal on the screened-in porch or patio. Bring your own boat and cruise the day away. Close to beaches - Stage Fort (5 min) and Good Harbor (12 min) as well as cafes, shops and nightlife in town center (10 min).

Top guest favourite

Home in Kittery Point

5 out of 5 average rating, 126 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 favourite

Home in Kittery

4.94 out of 5 average rating, 138 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!

Top guest favourite

Apartment in Rockport

4.98 out of 5 average rating, 182 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

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

Cottage in Kittery Point

4.98 out of 5 average rating, 42 reviews

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!