Condo vacation rentals in Gloucester

4.94 out of 5 average rating, 104 reviews

A spacious living area is highlighted by framed windows that provide ample natural light and offer views of the sky. A modern couch and an antique roll-top desk are present, accompanied by a cozy armchair. A decorative star design in the area rug adds a unique touch.

Condo in Peabody

Peabody Penthouse Top of the World Sunset View

Enjoy sunrise/sunset panoramic view from the new 6th floor Penthouse Sanctuary, the highest point in Peabody! This thoughtfully decorated spacious Penthouse open floor plan is a place to retreat, recharge, write, envision, and to enjoy the best of life. A walk away from the NS Mall/Borders Books where the Logan Express arrives. Also a mile away are the running trails, lovely ponds and apple picking at the city run Brooksby farm and six miles away from historic Salem. You will love it here!

A cozy outdoor patio features two bright red Adirondack chairs and a white circular table. The table holds two bowls of snacks and a glass of orange beverage. A backdrop of greenery creates a serene setting, enhancing relaxation.

4.96 out of 5 average rating, 178 reviews

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

Looking for the perfect Gloucester retreat for your group or family? Look no further than this spacious and inviting 2-bedroom unit, ideal for families and groups seeking comfort, style, and ample room to relax. Step inside and be greeted by a bright and spacious living area, perfect for gathering together after a day of exploring all that Gloucester has to offer. With its comfortable furnishings and modern amenities, this unit is designed to provide you with the ultimate vacation experience.

4.97 out of 5 average rating, 308 reviews

Seacoast Getaway

Seacoast, NH’s popularity is well-earned, with museums, the finest restaurants, spas and shopping that blend perfectly with the Seacoast landscape. From our beautiful beaches and coastline combined with plentiful outdoor recreation, including fishing and whale watching, kite flying and more with Portsmouth, Rye, Exeter and Kittery Maine, all a short ride our beachfront condo has something for all. After a day of outdoor activity and exploring, come retire and rest in our place with a view.

A modern kitchen is presented with crisp white cabinetry and sleek stainless steel appliances. A large island with seating for four is featured, providing a space for casual dining. Bright overhead lighting enhances the clean lines and organized layout of the kitchen.

4.98 out of 5 average rating, 126 reviews

1 Bedroom 1 Bath Waterview Downtown w/ Parking

Steps to ocean, steps to restaurants and shops. Quiet and quaint. Enjoy this centrally-located unit with all the town of Rockport has to offer right out the front door. Clean and fresh, with ocean views from the kitchen and living room. Unit has been renovated and updated with fresh paint, new appliances, new mattress and new sleeper sofa for guests. Enjoy the town shops, restaurants, sights, and beach all with a short scenic walk. This is Main Street, USA. Desirable Downtown Parking spot.

A comfortable living area features a sectional sofa arranged around a rustic coffee table. A floor lamp provides soft lighting, and decorative plants add a touch of greenery. Natural light enters through sheer curtains, illuminating an art piece on the wall.

4.88 out of 5 average rating, 153 reviews

Winter 3BR Escape | Historic + Modern Mix

Wisteria Vine Properties | Where comfort meets Salem’s magic. Discover this spacious and beautifully designed 3-bedroom, 2-bath condo—perfect for families and friend groups seeking a relaxing, memorable stay. Enjoy a fully equipped chef’s kitchen, hotel-quality beds, premium amenities, and a private outdoor space with BBQ. Just 7 min drive / 25 min walk to downtown Salem, the Witch Museum, and the House of the Seven Gables, and 8 min drive to the commuter rail for quick access to Boston.

Seating for two is positioned by expansive windows, offering views of the ocean and harbor at sunset. Natural light enhances the inviting atmosphere, while curtains frame the scene, highlighting the serene coastal setting.

4.95 out of 5 average rating, 111 reviews

Rockport Oceanfront Apartment 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!

A view of a waterfront building is framed by leafy tree branches. A staircase leads to a second-floor entrance. Brightly colored kayaks are lined up along the calm water's edge, with a wooden dock visible in the background.

4.98 out of 5 average rating, 123 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.

A private deck overlooks Rockport Harbor, featuring two white Adirondack chairs with turquoise cushions. The calm water is dotted with boats, and the iconic Motif #1 is visible in the background, enhancing the coastal ambiance.

4.99 out of 5 average rating, 210 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!

Condo in Lakeside Marblehead

A neutral-toned seating area features a modern gray couch adorned with throw pillows. A wooden coffee table sits in front, while a bedside table with a lamp and decor completes the cozy atmosphere. Large windows allow ample natural light into the space.

4.95 out of 5 average rating, 166 reviews

1742 Marblehead Studio|Minutes to Salem|Parking

Inquire about our winter rental rates! KEY FEATURES: ☀️Reserved parking for 1 vehicle ☀️Fully equipped + stocked kitchen ☀️New stainless steel appliances ☀️Light and bright space with four oversized windows ☀️Smart 4K TV ☀️Keurig with complimentary coffee ☀️Family Friendly! We provide pack and play, high chair, bouncer and stroller. No need to overpack with all of that baby gear! ☀️Futon that turns into a full sized bed ☀️Lots of natural lighting

A private bedroom features a spacious bed adorned with soft bedding in contrasting colors. Nightstands with lamps sit on either side. A vibrant neon sign is mounted on the wall, while the wooden ceiling beams add warmth. A colorful area rug completes the inviting space.

4.97 out of 5 average rating, 247 reviews

The Blue Suite, Private Parking Included

Welcome to The Blue Suite, a private condo within a historic home. The whole group will enjoy easy access to everything from this centrally located place. Just under a half a mile to all tourist attractions in Downtown Salem, but far enough away to be peaceful at night. Also a half mile from the commuter rail and a 40 minute ride from the airport. This listing includes one parking spot in an on site privately owned parking lot.

4.95 out of 5 average rating, 139 reviews

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!

An open living space features hardwood floors and a modern aesthetic. A sleek fireplace is mounted on the wall beneath a flat-screen TV. Bar stools with orange upholstery are positioned at the kitchen island, and a glass coffee table sits on a patterned area rug.

4.98 out of 5 average rating, 110 reviews

Boho Beach Condo for Ocean Escape

Enjoy a stylish experience at our centrally-located oceanfront condo. We are walkable to exquisite beaches and parks as well as downtown Gloucester where you will find a number of bars and restaurants to explore. If you feel like hanging in, share a meal/cocktail on the private deck. Perfect for a couples getaway or a group of friends looking to explore the North Shore without ever getting in your car.

Popular amenities for Gloucester condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.91 out of 5 average rating, 498 reviews

The living room features a grey sofa adorned with blue accent pillows, paired with two blue chairs. A coffee table with a glass top sits in front, and light enters through windows with white shutters. The hardwood floor adds warmth to the space.

Condo in Beacon Hill

BEAUTIFUL BEACON HILL 2 BEDROOM!

5 out of 5 average rating, 20 reviews

Witch City Nook - AC, Parking, Walk Everywhere!

5 out of 5 average rating, 47 reviews

A serene landscape showcases a sprawling marsh at sunset, with vibrant hues in the sky. Tall grasses and slender trees frame the scene, while a gentle waterway meanders through the lush greenery, providing a tranquil backdrop.

Condo in Essex

Marshside one-bedroom with stunning view

4.77 out of 5 average rating, 26 reviews

Marina View, Walk to Niles Beach & Rocky Neck

A small workspace features a marble-top table accompanied by a white chair with a fur throw. The green wall displays a variety of framed artwork and a small chalkboard with the word 'Welcome.' A mirror above the table reflects elements of the cozy room.

5 out of 5 average rating, 76 reviews

The Merchant's Carriage House - Downtown Salem

The bright studio condo features a spacious bed with soft linens and a cozy armchair alongside. A small table is placed near the well-equipped kitchen area, while large sliding glass doors provide views of the marsh. Natural light fills the room, enhancing the welcoming ambiance.

4.88 out of 5 average rating, 65 reviews

Top Floor Beach Condo with Fabulous Sunset Views.

A bright living area is highlighted by slanted skylights and large windows, offering abundant natural light. Two comfortable armchairs and a spacious blue sofa accompany a wooden coffee table, while a dining table with white chairs sits in the corner. Decorative elements include a plant and framed artwork.

4.99 out of 5 average rating, 75 reviews

Panoramic Ocean Views in Rockport

A spacious porch features outdoor seating arranged around a wicker coffee table, with views of Gloucester Harbor visible in the background. The sky is partly cloudy, allowing natural light to illuminate the wooden deck. Railings surround the area, providing a sense of openness.

4.95 out of 5 average rating, 42 reviews

Retreat to tranquility - water views

Pet-friendly condo rentals

4.85 out of 5 average rating, 139 reviews

A sleek kitchen features modern stainless steel appliances, including a gas stove and a kettle. White cabinetry complements the glossy white subway tile backsplash. Light reflects off the countertops, enhancing the bright and clean appearance of the space.

Condo in Watertown

Nice Condo to Harvard, MIT, Fenway, with parking

4.93 out of 5 average rating, 226 reviews

The living area features two gray sofas positioned around a round wooden coffee table on a vibrant blue area rug. A cozy fireplace is situated against a striking red wall, complemented by a bookshelf filled with books. Natural light enters through a nearby window.

Condo in East Boston

Family Home + Near Downtown + Cool Backyard!

4.87 out of 5 average rating, 124 reviews

The living room features wooden floors with a patterned area rug. Comfortable seating is arranged, including a gray sofa and two armchairs. Natural light pours in through multiple windows, and a decorative lamp stands beside a framed art piece on the wall.

Condo in Roslindale

Transit friendly condo on quiet street

4.95 out of 5 average rating, 114 reviews

A spacious living area is shown, featuring a light-colored sectional sofa, an accent chair, and a wooden coffee table. Natural light filters through large sliding doors, which open to a private deck. A soft area rug lies beneath the furniture, enhancing the cozy atmosphere.

Condo in South Boston

Boston Townhouse - 3bd / 2.5ba - Central Location

Condo in Lakeside Marblehead

A comfortable living room features a soft gray sofa flanked by two armchairs. A round coffee table sits in the center, adorned with a decorative bowl. Natural light enters through a window adorned with white shutters, and a cozy rug enhances the inviting ambiance.

4.98 out of 5 average rating, 196 reviews

Harbor Hideaway

4.93 out of 5 average rating, 194 reviews

An open living space features a modern gray sofa paired with a dark green accent chair. A round coffee table sits on a textured blue rug. Natural light enters through large windows, illuminating the dining area and kitchen with stainless steel appliances and wooden cabinets.

Condo in Waltham

New Super Modern 2 bed in Waltham

Superhost

A well-lit bedroom features a spacious bed dressed in crisp white linens, flanked by small bedside tables with lamps. Large windows provide natural light and views of the surrounding area, while the soft blue walls create a calming ambiance.

Condo in South Boston

4.87 out of 5 average rating, 121 reviews

Penthouse 2 Beds /2 Baths luxury in South Boston

4.94 out of 5 average rating, 186 reviews

A modern kitchen is showcased with light wood cabinetry and an expansive island featuring a white marble countertop. Pendant lights hang above, illuminating the space. The open layout leads to a cozy living area with a large sectional sofa, surrounded by windows that invite natural light.

Condo in East Boston

Luxury apt w/ sauna & deck | by airport, downtown

Condo rentals with a pool

5 out of 5 average rating, 22 reviews

A sandy beach at sunset is depicted, with soft waves gently lapping against the shore. Large, smooth rocks are positioned in the foreground, reflecting the warm orange and golden hues of the sun dipping below the horizon.

Condo in Hampton

Lovely 2 BR beach condo with inground pool

A stone statue of a woman is depicted sitting gracefully, holding a wreath. An American flag flutters above, while a multi-story building is visible in the background, suggesting a seaside location.

4.9 out of 5 average rating, 41 reviews

Hampton 100 yards to beach

A view of the ocean is framed by large windows, displaying tranquil blue waters and sandy beaches. The image captures the shoreline and nearby buildings, offering a glimpse of the vibrant beach atmosphere.

4.98 out of 5 average rating, 47 reviews

Ocean View - Steps to the Beach!

4.91 out of 5 average rating, 11 reviews

A newly renovated studio features a spacious bed with a leaf-patterned comforter. A wooden wardrobe stands against the wall, complemented by a mounted flat-screen TV. Soft lighting is provided by wall sconces, creating a cozy atmosphere. A seating area with a small table is visible.

Condo in Hampton

Hampton Beach Bailey's Resort

An aerial view of Hampton Beach highlights the proximity of the condo to the beach and nearby attractions. The coastline stretches out with sandy shores and a vibrant blue ocean. Nearby buildings and roadways are visible, providing a sense of the community and access to the area.

4.84 out of 5 average rating, 100 reviews

Steps from Beach | 2BR Monthly | Parking

A bottle of 406 Co. Cellars wine rests on a wooden table beside two clear wine glasses. A decorative blue sign reading 'Hampton Beach' adds a touch of local charm to the setting. Soft lighting creates a warm ambiance.

4.98 out of 5 average rating, 85 reviews

406 Co. Seascape

4.81 out of 5 average rating, 57 reviews

The image shows a sandy beach with gentle waves lapping at the shore. Surfers can be seen in the water, navigating the rolling waves under a cloudy sky. The horizon blends the ocean and sky in soft shades of blue and gray.

Condo in Hampton

Beachn' at North Beach

A quaint bedroom features a queen size bed dressed with a floral patterned comforter. Two bedside lamps provide soft lighting, and a small refrigerator is positioned next to the bed. A television is mounted on the wall, and a colorful painting adds visual interest.