Condo holiday rentals in Gloucester

4.96 out of 5 average rating, 179 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 airy living area🛋️, perfect for gathering together after a day of exploring all that Gloucester has to offer 🚤🏞️. With comfortable furnishings 🪑 and modern amenities📺🍽️, this unit provides the ultimate vacation experience🌴🍹.

4.94 out of 5 average rating, 106 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 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 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.

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!

4.97 out of 5 average rating, 275 reviews

An open living area showcases a warm ambiance with string lights overhead. A dining table is set for six, and a cozy seating arrangement includes a colorful armchair and a plush sofa. A wall-mounted TV is positioned beside vibrant artwork against the white walls.

Condo in Salem

*1710 Historic 2BR Retreat|Downtown Salem|Parking

🏆 Top 1% property in Salem! Welcome to The Archer House — your cozy winter retreat! This 2-bedroom apartment offers free parking for 2 cars and all the comforts for a warm, relaxing stay. Just steps from the Salem Witch Museum and downtown’s seasonal attractions, it’s the perfect winter escape for travelers! ❄️ 🧙🏻‍♀️ Salem Witch Museum - 3 min walk 🎃 Witch House - 10 min walk ✨ Downtown Salem - 1 Min walk 🕸 Hocus Pocus House - 5 min drive

A spacious game room features a stylish hanging chair and a classic arcade machine in the background. Natural light illuminates the wood-paneled ceiling and bright walls, creating a welcoming space ideal for family fun or relaxation.

4.99 out of 5 average rating, 136 reviews

3BR Oceanfront Condo with decks

Have fun with the whole family at our stylish oceanfront condo. Capture exquisite sunrises and sunsets off of the decks overlooking the ocean. Spend time in the spacious arcade/game room with family and friends or listen to some smooth beats using our retro record player. Walk to downtown Gloucester where you will find a number of restaurants and bars or alternatively walk to exquisite beaches or parks all available steps from your front door.

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!

4.98 out of 5 average rating, 130 reviews

An open kitchen-living area features a large central island with dark cabinetry and a light countertop. Stylish pendant lights hang above the island. A comfortable seating area is visible, with natural light filtering through large windows and doors that lead to an outdoor space.

Condo in South Boston

Perfectly Renovated Home w/ Private Outdoor Oasis

COMPLETELY PRIVATE - NO SHARED SPACE OTHER THEN WASHER/DRYER AREA IN BASEMENT! Enjoy a private kitchen, 2 bedrooms, 2 baths and private outdoor space. The Master Bedroom has a king Bed with an ensuite bathroom. The Second Bedroom has a queen bed, gas fireplace and is right across from the second full bath. PARKING IS NOT INCLUDED. **outdoor furniture will be put away for the Winter in November & reassembled mid-May*

4.93 out of 5 average rating, 131 reviews

A cozy living area is situated under the inclined ceiling, featuring a corner couch and an armchair. A television is positioned on a light-colored media console. A skylight allows natural light to fill the room, illuminating the hardwood floors.

Condo in Salem

Lovely Condo-close to Downtown Salem 1bed/1ba

Welcome to your ideal location for all things Salem. As you enter this comfortable fully equipped 1 bedroom condo you will feel right at home. Tastefully furnished and centrally located yet on a very quiet side street. This lovely condo will make your North Shore visit memorable!

4.9 out of 5 average rating, 115 reviews

An open concept living area features a cozy sofa, a round coffee table with decorative items, and a dining area. A spacious bed is visible through an archway, surrounded by natural light from multiple windows. Charming period details are present throughout the space.

Condo in Newburyport

Newburyport Apartment Suite

Have fun with the whole family at this historic, spacious, open concept apartment suite. Full kitchen and bath. Private outdoor patio with table and umbrella. Less than 1 mile walk to downtown. 5 minute drive to Plum Island.

Popular amenities for Gloucester condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.92 out of 5 average rating, 839 reviews

A modern living area features a black leather sofa paired with decorative pillows. A white area rug lies beneath a coffee table, complemented by an accent chair with a geometric pattern. Natural light filters through the two windows, creating a bright and inviting space.

Condo in Cambridgeport

Spacious 2 bedrooms Apt -Roof deck NO Cleaning fee

4.99 out of 5 average rating, 107 reviews

A living area features a contemporary black sofa and two matching armchairs arranged around a round glass coffee table, all placed on a vibrant blue rug. A large artwork hangs on the wall, and a window allows natural light to enter the space.

Condo in South End

1 Bedroom Apartment in Boston/South End

4.84 out of 5 average rating, 149 reviews

Walk to beach, heart of Hampton Beach

Superhost

A well-lit bedroom contains a queen bed with white linens and two neatly folded towels placed at the foot. Two windows provide natural light, while a decorative chandelier hangs from the ceiling. A small lamp and a console table are positioned nearby.

Condo in Cambridgeport

4.86 out of 5 average rating, 1,061 reviews

Private studio w/ parking by MIT/Harvard/BU/Fenway

Superhost

The kitchen area features wooden cabinetry and stainless-steel appliances, including a refrigerator and a new range. A spacious island with bar seating is complemented by a small dining table. Natural light enters through multiple windows, highlighting the indoor plants present.

5 out of 5 average rating, 8 reviews

Sunny Condo

4.87 out of 5 average rating, 108 reviews

A modern studio living area is showcased with a comfortable gray sofa positioned beside a wooden coffee table. A flat-screen TV is mounted on the wall opposite a compact kitchenette, featuring a fridge and sink. Soft lighting is provided by a nearby lamp, creating an inviting ambiance.

Condo in Arlington

Lovely Studio - Spotless, W/D, Parking, Private

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

4.91 out of 5 average rating, 187 reviews

A cozy living area is presented with a light wooden floor and recessed lighting. A circular coffee table sits on a soft area rug, surrounded by a blue armchair and white accent chairs. Bookshelves with decorative items line one wall, contributing to the modern aesthetic.

Condo in Cambridge

Pretty private garden-level condo+parking near MIT

Pet-friendly condo rentals

4.88 out of 5 average rating, 144 reviews

A bright living area is highlighted by a circular dining table surrounded by four chairs. A large round mirror above a white fireplace reflects the light. Warm wooden floors contrast with the cream walls, accentuated by subtle decor elements and natural light from nearby windows.

Condo in Bay Village

Condo in downtown Boston

4.84 out of 5 average rating, 257 reviews

The living room is furnished with a brown leather sofa and a light-colored sectional, surrounded by multiple windows allowing natural light. A dark wooden coffee table is placed centrally, adorned with a decorative bowl. An accent chair and a white cabinet add to the room's functionality.

Condo in East Somerville

A Cozy 3BR Home Close To Train + Boston & Parking

4.87 out of 5 average rating, 126 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

4.89 out of 5 average rating, 577 reviews

A historic brick brownstone is shown from the street, featuring a classic architectural style with bay windows. The building is framed by vibrant green trees and neatly trimmed bushes, contributing to the residential charm of the neighborhood.

Condo in Jamaica Plain

Historic JP Brownstone with Parking. Pets Welcome!

4.83 out of 5 average rating, 245 reviews

A comfortable outdoor seating area is presented on a covered porch. The space features a sectional sofa and four wicker chairs arranged around a glass coffee table. Views of nearby buildings and a clear blue sky can be seen in the background, enhancing the serene environment.

Condo in Winter Hill

Spacious, cozy home near Boston!

4.95 out of 5 average rating, 115 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

4.92 out of 5 average rating, 195 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

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

Condo in Portsmouth

4.71 out of 5 average rating, 21 reviews

2BR Balcony, Parking, Pool, Hot Tub, Tennis!

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

Superhost

An open living area is visible, featuring a gray sofa, a patterned yellow armchair, and a dining table with six chairs. Large sliding glass doors provide access to a balcony, offering views of the outdoors. A kitchen counter and a coffee machine are also present.

Condo in Hampton

4.81 out of 5 average rating, 32 reviews

Serenity by the Sea

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 | Pool | Parking | Large Deck

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.