Places to stay near Cressy Beach

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Top-rated holiday rentals near Cressy Beach

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Guest favourite
French doors open into a cozy living area where a sectional sofa is visible. A small green table with a bouquet of flowers sits in front, while sunlight illuminates the space. Outside, garden views reveal lounge chairs and vibrant flowers.
Guest house in Gloucester
4.96 out of 5 average rating, 289 reviews

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

Guest favourite
An expansive view of the ocean showcases rolling waves under a partially cloudy sky. A deck is visible, outfitted with outdoor seating, surrounded by lush greenery and coastal vegetation, creating a serene outdoor space.
Flat in Gloucester
4.86 out of 5 average rating, 121 reviews

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

Guest favourite
A charming white house is positioned along a rocky shore, showcasing a four-season porch with large windows that provide views of the harbor. Lush greenery surrounds the property, complementing the tranquil water scene with boats in the distance.
Home in Gloucester
4.93 out of 5 average rating, 171 reviews

Wonderful Rocky Neck home on Gloucester harbor

2 Bedroom with Loft, 1 Bathroom fully furnished Home on Gloucester harbor. Dead end street with 3 off street parking spots. Restaurants, local art gallery's, the beach all just a short walk away. Wake up with the sweet smell of ocean air and the sound of seagulls calling. Enjoy your breakfast with a million dollar view on the 4 season porch with 8 sliding windows overlooking the harbor. You could spend hours watching the boats go by as you read a good book with your fur baby on your lap.

Guest favourite
The exterior view of the home reveals a modern wooden structure surrounded by lush greenery. A spacious deck extends from one side, while stone pathways weave through well-maintained gardens. Soft blue skies and gentle clouds create a serene atmosphere.
Home in Gloucester
4.97 out of 5 average rating, 143 reviews

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

Guest favourite
A modern living area features a light-colored sofa adorned with decorative pillows and a natural wooden coffee table. A round mirror reflects light, while a small wooden side table and a potted plant add a touch of greenery. Soft ambient lighting enhances the soothing atmosphere.
Flat in Gloucester
4.96 out of 5 average rating, 139 reviews

Beautifully remodeled unit in heart of Gloucester

Enjoy your stay in the heart of Gloucester close to everything this great town has to offer. This unit was completely remodeled in 2022. Two shorts blocks from Main Street in Gloucester and all of its wonderful restaurants and shops. Three blocks from the Beauport Hotel - perfect for wedding guests not staying at that location. This unit has new floors, countertops, appliances and fixtures and is freshly painted (no VOC paint). You will love this unit and location for your visit.

Top guest favourite
A welcoming sign for the Rocky Neck Art Colony is displayed prominently. The sign features blue and white colors with decorative elements, including an image of a bird. Text indicates the area is one of America's oldest working art colonies, situated in historic Gloucester.
Loft in Gloucester
4.92 out of 5 average rating, 227 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2025! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

Top guest favourite
A bright living area features large windows allowing natural light to fill the space. A comfortable sofa and a cozy armchair sit on a patterned rug, with a wooden coffee table in between. A dining table is visible in the background, creating a welcoming atmosphere.
Flat in Gloucester
4.94 out of 5 average rating, 125 reviews

Walk to Good Harbor Beach

Newly renovated ground floor efficiency apartment with sliders/walkout to fenced backyard. Wifi and Netflix included. Most dogs okay, some breed restrictions apply. If you want to bring your dog please contact us prior to booking. Three night minimum for all stays. Space includes 1 bedroom with Queen size bed and Living Area with pull out couch. 2 adults will be most comfortable. 5 minute walk to Good Harbor Beach or Bass Rocks. 15 minute walk to Rocky Neck.

Top guest favourite
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.
Apartment in Gloucester
4.99 out of 5 average rating, 128 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.

Top guest favourite
An aerial view captures a spacious coastal home, surrounded by lush trees with changing leaves. The structure showcases a wraparound deck, and the sloped lot offers a rocky edge, enhancing the natural setting. Nearby residences are partially visible through the foliage.
Flat in Rockport
4.93 out of 5 average rating, 172 reviews

Hidden Gem! Short term rental steps from 2 beaches

Hidden Gem! Short term seaside rental. Lovely 1 bed 1 bath unit located on private wooded property, steps away from 2 beaches. Private unit amenities include deck with gorgeous year round views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.

Top guest favourite
A cozy sleeping area features a queen bed with decorative pillows and a textured blanket. Two large windows provide natural light, while a charming quilted wall hanging adds character. A wooden dresser and seating area with wicker chairs enhance the inviting atmosphere.
Guest suite in Rockport
4.98 out of 5 average rating, 718 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

Guest favourite
The exterior entrance features a charming black door beneath an elegant archway. Flanked by decorative planters and surrounded by thoughtfully trimmed greenery, the light blue siding of the building presents a welcoming appeal. The name 'GILBERT' is displayed prominently above the entrance.
Flat in Gloucester
4.97 out of 5 average rating, 168 reviews

The Gilbert: 1-Bed downtown suite, walk to beach.

Come stay in Gloucester’s historic downtown district, in St. Peter’s Square, just one block from Pavilion Beach, Stacey Boulevard and the historic West End of Main Street. The Gilbert sleeps two (up to 3 with an air mattress). A perfect getaway for those in love with history and seaside living. The unit has a private entrance, king sized bed, kitchenette and private bath.

Guest favourite
A bronze statue depicting a fisherman gripping a ship's wheel stands prominently against a backdrop of a colorful sunset. The scene includes gently rippling waters and nearby flags fluttering in the breeze, creating a serene atmosphere typical of coastal towns.
Flat in Gloucester
4.79 out of 5 average rating, 256 reviews

Prime location to Beauport Hotel & Beach, Glo Apt

Located in the heart of historic Gloucester this two bedroom, fully furnished apartment is a 5 minute walk to the Beauport Hotel, beach, museums, shops, restaurants, train , boat shuttle, the famous "Man at the Wheel" Statue and much more. Dunkin Donuts and a mini mart on the same street. . Please inquire about transportation options. Best Location on the island!

Popular amenities for holiday rentals near Cressy Beach

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Essex County
  5. Gloucester
  6. Cressy Beach