Gloucester vacation rentals

4.87 out of 5 average rating, 109 reviews

A serene morning on the lake is depicted, with two individuals paddling a kayak through mist-covered water. The surrounding landscape features dense trees and gentle hills, while soft light reflects off the calm surface, creating a peaceful atmosphere.

Vacation home in Natick

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

4.9 out of 5 average rating, 129 reviews

A sandy pathway leads through wooden fencing towards the ocean. Soft grasses frame the path, and the blue sea is visible in the distance under a clear sky filled with scattered clouds.

Home in Salisbury

NEW 3BR home, incredible views - Beach across St

Enjoy sunrises and sunsets with an expanse of windows that offer breathtaking views of the river and marsh in a new construction, BEAUTIFUL, single family home. Over 2000 Sq Ft wTile & hardwood floors. 1st level has Open living room/kitchen, half bath & 1 bedroom. 2nd Floor has 2 bedrooms, bath, laundry & Large outdoor deck. Beach is a 2 minute walk across the street. 10 minutes to Browns Seafood restaurant, Ice Cream, Groceries & more. 2+ Parking spots. We follow the Advanced Clean Protocol.

4.96 out of 5 average rating, 303 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

4.84 out of 5 average rating, 111 reviews

An outdoor seating area features bright orange Adirondack chairs arranged around a fire pit, complemented by a shaded area provided by a large umbrella. The cottage is visible in the background, showcasing its coastal charm with fresh landscaping enhancing the inviting space.

Cottage in Newbury

Designer decorated-Sunset Bliss- Beach 3 min walk

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk the cottage for ice cream, Rip tide & the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

4.87 out of 5 average rating, 111 reviews

A private wrap-around porch is shown, featuring a wooden dining table with matching chairs. Sunlight filters through, illuminating the surrounding neighborhood with cozy homes and greenery visible in the background. The space is complemented by a decorative plant on the table.

Apartment in Swampscott

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

4.86 out of 5 average rating, 122 reviews

A charming exterior view features a two-story house with light grey siding and a red wooden staircase. Lush greenery surrounds the property, including flowering trees. A brick walkway leads to the front entrance, inviting visitors into the home.

Apartment in Amesbury

Private, 2bd, 1st floor unit in historic Amesbury

Your family will be close to everything when you stay at this centrally-located Antique New England getaway . Recently renovated, but tastefully original. Everything you need is within walking distance; shopping, grocery, dining, lake, short drive/ride to beach. The space is about 900sqft; 1 bathroom, king bedroom, queen bedroom, queen pull-out couch, and an additional room in which a twin bed can be put (upon request). It will comfortably hold 4 adults, but will accommodate up to 7.

Guest suite in Kittery Point

A round mirror with a wooden frame is positioned in front of a glass-enclosed walk-in shower. The shower features a modern showerhead and a tiled wall, providing a clean and contemporary look.

4.95 out of 5 average rating, 289 reviews

Romantic Spa By The Ocean. Hot Tub. Walk to Dining

Just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub on your private patio. Feet-up pampering and special gifts throughout this adorable Maine coastal getaway. Drive into Portsmouth, or stay-in and pamper yourselves. Walk to the Kittery Point town wharf, historical sites, the Bistro and Wharf Restaurant, and catch views of the lighthouse and spectacular sunsets. 5-minute drive to a beach or world-class restaurants, 10-min to the famous Kittery Outlets.

5 out of 5 average rating, 126 reviews

The bedroom features large sliding glass doors that open to a private balcony, showcasing expansive views of the water and surrounding landscape. Soft natural light fills the room, highlighting the simple yet modern decor and comfortable bedding.

Home in Kittery Point

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!

4.93 out of 5 average rating, 115 reviews

A comfortable bedroom features a spacious bed covered in a neutral-colored quilt. Natural light fills the room through large windows offering views of the private pool and surrounding landscape. A white chair and open closet add to the room's functionality.

Cottage in Newburyport

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.

An expansive porch features a circular wooden table surrounded by pastel blue chairs. A colorful patterned rug anchors the seating area, with decorative string lights overhead enhancing the space. Lush greenery is visible in a planter, adding a touch of nature.

4.81 out of 5 average rating, 186 reviews

Steps to Beach Fireplace Pat's Porch

Welcome to Pat's Porch, the sister cottage of Lorraine's Landing and a professionally managed beach getaway - Just a 5-minute stroll from the sun-kissed shores and bustling boardwalk of Hampton Beach, this 3-bedroom, 1-bath abode boasts a queen master bedroom and newly updated kitchen. Relax on the expansive porch equipped with a picnic table, lounge chairs, and grill, or unwind indoors with fast wifi and a Samsung Smart TV.

4.84 out of 5 average rating, 106 reviews

A rooftop deck offers a view of the ocean and colorful sunset skies. Comfortable outdoor seating is positioned on the wooden deck, allowing for relaxation while enjoying the scenery. Nearby greenery and the road leading to the beach are visible in the foreground.

Home in Rye

"The Surf" Ocean & Marsh Views Rooftop Deck

Welcome to "The Surf", Rye's ultimate private vacation home. You'll love the views from your bedroom and rooftop deck being directly across the street from the ocean. Lots of back-yard fun to be had or simply enjoy relaxing on the first-level deck while looking out at the marsh. Centrally located to Jenness Beach, Wallis Sands State Beach and Rye Harbor, this single-level property makes for the perfect coastal getaway.

4.96 out of 5 average rating, 100 reviews

A well-maintained outdoor area is highlighted, featuring a grassy lawn leading up to stone steps. The house, adorned with dark siding, is framed by a large tree and offers a welcoming seating arrangement on the porch. Clear skies provide ample natural light.

Condo in Gloucester

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

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Popular amenities for Gloucester vacation rentals

Laptop-friendly workspace

Stay near Gloucester's top sights

Wingaersheek Beach66 locals recommend

Crane Beach124 locals recommend

Good Harbor Beach118 locals recommend

Halibut Point State Park115 locals recommend

Rockport Music-Shalin Liu Performance Center77 locals recommend

Cape Ann Museum69 locals recommend

Gloucester beach vacation rentals

4.86 out of 5 average rating, 178 reviews

Colorful stacked kayaks are arranged on a grassy area overlooking the water. A sandy beach is visible in the foreground, leading to a stone jetty extending into a calm body of water. A clear blue sky with scattered clouds fills the background.

Home in Beverly

Beverly Beach House- Upper Deck

The exterior of the cottage is visible, featuring light gray siding and multiple windows with white trim. A vibrant display of pink flowers is situated in the foreground, providing a colorful contrast to the structure.

4.96 out of 5 average rating, 273 reviews

2 Bedroom Beach Bungalow, Steps from the Beach!

4.76 out of 5 average rating, 82 reviews

A charming ranch-style home is showcased with a blue front door and classic window shutters. Two light-colored chairs are placed on the manicured lawn, surrounded by vibrant pink flowers. The entrance is framed by white railings and a well-maintained pathway.

Home in Seabrook Beach

Beach Bums' House - Perfect for Families & Friends

4.98 out of 5 average rating, 154 reviews

A serene beach scene showcases soft waves gently lapping against the shoreline. Light sand is dotted with smooth rocks, while the horizon features clear blue skies meeting the ocean. A few distant figures can be seen enjoying the beach, contributing to a peaceful atmosphere.

Condo in Hampton Beach

Beachfront Getaway

4.86 out of 5 average rating, 114 reviews

The exterior of a white and blue two-story house is showcased, featuring a sign that identifies the property. Black shutters frame the windows on the upper floor, while a white picket fence surrounds the front yard. A car is parked along the side of the building.

Apartment in Salisbury

Ocean Wave unit, Melo's Beach House Rentals

4.94 out of 5 average rating, 111 reviews

An outdoor balcony is furnished with wooden seating and a coffee table, providing ocean views and a serene atmosphere. The nearby sandy beach can be seen in the background, framed by a clear blue sky and a gentle horizon.

Condo in Hampton Beach

Summer bliss in our oceanfront 2BR condo awaits!

4.99 out of 5 average rating, 165 reviews

Cottage in Newburyport

True North Cottage*Ocean side of Boat Basin!*

4.97 out of 5 average rating, 267 reviews

A serene sunset is captured over the horizon, with a vibrant gradient of orange and yellow hues illuminating the sky. Smooth, dark stones dot the foreground, reflecting the warm colors of the sunset, creating a calm, tranquil atmosphere at the water's edge.

Condo in Hampton Beach

Beachfront Summer Fun

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Gloucester house rentals

The exterior of a multi-story coastal building is displayed during twilight. Soft lighting illuminates the balconies, which feature green chairs. A fence encloses the property, and neighboring structures are faintly visible in the background.

4.94 out of 5 average rating, 105 reviews

Pearls on Perkins, Beautiful Condo!

4.99 out of 5 average rating, 129 reviews

A modern living area features vaulted ceilings and wooden accents, creating an open atmosphere. A large flat-screen television is mounted on a white media console. Comfortable seating is provided on a dark sectional sofa, complemented by natural light from skylights and windows.

Home in Newburyport

“Salty Girl” Plum Island, MA

4.96 out of 5 average rating, 293 reviews

The Victorian-style home features a welcoming front porch and a well-maintained garden with various plants and flowers. The two-story structure has a sloped roof and is surrounded by trees, providing character and charm to the exterior.

Home in Somerville

Best House Cambridge/Somerville

4.92 out of 5 average rating, 119 reviews

A mid-century house is positioned among lush greenery, showcasing a modern exterior in muted tones. A paved driveway leads up to the entrance, framed by a natural landscape of trees and grass, creating a serene and inviting outdoor environment.

Home in Lexington

Mid-Century Modern in Historic Lexington

4.88 out of 5 average rating, 147 reviews

The living room is designed for relaxation with a comfortable sofa and a flat-screen TV. Natural light fills the space through large windows, illuminating the hardwood flooring. A center coffee table enhances the inviting atmosphere, encouraging gatherings after a day of exploring.

Home in Quincy

284 - New! Tranquil & Cozy Boston Home

4.98 out of 5 average rating, 194 reviews

A fire pit is surrounded by colorful adirondack chairs in a grassy area, with bright yellow flowers adding a pop of color. The view in the background includes a landscape of greenery leading to the water, suggesting a peaceful outdoor space for gatherings.

Home in Ipswich

Stagehill Beach House

4.96 out of 5 average rating, 114 reviews

A classic staircase with rich wooden handrails leads to the upper levels. A small console table beside the stairs features decorative items, including a flower vase and framed wall art with welcoming messages. The rustic accent wall adds charm to the entryway.

Home in Dorchester

LargeDuplex10Beds w/prkg near Downton

4.88 out of 5 average rating, 135 reviews

A spacious living area features modern appliances, including a stainless steel refrigerator and stove. Soft-toned cabinetry complements the kitchen space. Comfortable seating is provided by a sectional sofa with contrasting cushions, while natural light floods in through multiple windows.

Home in Woburn

Large 4Bed 2Bath Clean Alternative to Hotel Living

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Beach house rentals in Gloucester

5 out of 5 average rating, 19 reviews

The exterior of a beach house is displayed, featuring light gray shingles and a white railing. A spacious covered front deck and multiple large windows create an inviting entrance. Stairs lead up to the double front doors, framed by additional windows on either side.

Home in Rockport

Oceanfront Home Rockport

4.97 out of 5 average rating, 71 reviews

A scenic view of the backyard faces the pond, featuring a well-maintained lawn and a firepit area. Several seating options are visible, including white Adirondack chairs and a red bench. Lush trees provide shade, framing the home and enhancing the tranquil outdoor space.

Home in Scituate

Well Scituated

4.99 out of 5 average rating, 100 reviews

An open living area features a hardwood floor that connects the dining space with large windows and comfortable seating. A wooden dining table with chairs is positioned at the center, while a black cabinet stands against the wall near a decorative fireplace.

Home in Scituate

4BD Quiet Sand Hills Beach House

4.91 out of 5 average rating, 53 reviews

A charming exterior view showcases a two-story home surrounded by lush greenery and vibrant white flowers. A spacious wrap-around deck is visible, offering access to the entry. Sunlight highlights the textured siding, creating an inviting atmosphere in the peaceful neighborhood.

Home in Rye

*Ocean View* Charming beach house

4.94 out of 5 average rating, 18 reviews

Updated Beach House One Block From the Beach

4.95 out of 5 average rating, 41 reviews

Beach access, walking distance to downtown!

4.94 out of 5 average rating, 97 reviews

An open kitchen and dining area are featured, showcasing a modern stainless steel appliance set and a spacious wooden dining table surrounded by six chairs. A blue glass vase is placed at the center of the table. Light hardwood flooring is visible throughout, contributing to the bright atmosphere.

Home in Salisbury

Gorgeous 4 bedroom beach house. Perfect location!