Family-friendly vacation rentals in Gloucester

4.96 out of 5 average rating, 197 reviews

Condo in Gloucester

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🌴🍹.

KitchenFamilyCondition

4.96 out of 5 average rating, 310 reviews

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.

Guesthouse in Annisquam

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

KitchenFamilyGetting around

4.99 out of 5 average rating, 172 reviews

The open kitchen features a large island with seating for several guests. A cozy living area is visible, with a comfortable seating arrangement and large windows allowing natural light and ocean views. Warm wood flooring complements the airy atmosphere.

Apartment in Rockport

4 Bed Water View w/ Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

Indoor spacesKitchenBathroom

4.86 out of 5 average rating, 138 reviews

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.

Apartment in Gloucester

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.

KitchenIndoor spacesGetting around

4.93 out of 5 average rating, 190 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.

Indoor spacesKitchenCondition

4.93 out of 5 average rating, 123 reviews

A quaint stone cottage is surrounded by lush greenery and colorful flowers, with a well-maintained garden featuring clusters of purple blooms. The cottage's rustic charm is complemented by a sloped lawn and mature trees, creating a serene outdoor atmosphere.

Guesthouse in Gloucester

Plum Cove Cottage with king suite!

A quaint 1900's cottage Plum Cove beach is just 500 ft away! The full gourmet kitchen has granite counters and stainless steel appliances. There is also a spa shower, romantic king bedroom with maple spiral stairs and 3 skylights which provide amazing light throughout. Watch the spectacular sunsets voted one of the best in the world by National Geographic. This is the premier location to begin your exploration of Cape Ann. Beach umbrellas and chairs provided.

FamilyIndoor spacesParking

4.97 out of 5 average rating, 497 reviews

A charming log cabin is surrounded by lush greenery. Two miniature horses graze leisurely on the grass in front of the cabin, which features a covered porch and simple landscaping with flowers. Sunlight filters through the trees, highlighting the serene woodland setting.

Cabin in Rockport

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

FamilyKitchenGetting around

A panoramic view reveals the tranquil ocean, with soft waves lapping against the shore. Green trees and distant sandy areas are visible, enhancing the natural scenery. Several rooftops in the foreground provide a sense of elevation and perspective towards the coastline.

4.98 out of 5 average rating, 111 reviews

Ocean views! Welcome to Sea Breeze! Winter rates!

Sea Breeze offers a spacious, newly renovated, 4 bedroom escape, that smiles down upon Good Harbor beach. Take in the refreshing salt air breezes while enjoying the solitude of being situated at the end of a quiet cul de sac. A short 3-5 minute drive gets you into the Good Harbor parking lot or take a 20 minute walk instead. Close-by downtown Gloucester is teeming with spectacular restaurants and activities for the whole family.

FamilyKitchenComfort

4.93 out of 5 average rating, 101 reviews

The exterior of a two-story house is surrounded by lush green shrubs and blooming white daisies. A small outdoor seating area is visible, featuring two green chairs and a table set for refreshments. Natural light illuminates the inviting entrance, enhancing the welcoming appearance.

Home in Rockport

Family Friendly Home|Walk to Ocean+Downtown RKPT

KEY FEATURES: ☀️Full home with 2 levels and private yard with BBQ ☀️New AC mini split system for hot summer days ☀️Newly remodeled bathroom with walk in shower ☀️Fully equipped kitchen ☀️Washer and dryer ☀️Hi-speed WiFi ☀️Family Friendly Amenities - pack and play, high chair, toys, and more! ☀️2 parking spots ☀️Beach essentials provided in the shed- chairs, beach towels, toys and more! ☀️Board games and books

Indoor spacesKitchenGetting around

4.97 out of 5 average rating, 139 reviews

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.

Condo in Gloucester

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.

KitchenIndoor spacesParks

4.89 out of 5 average rating, 148 reviews

An open-concept living area is highlighted by a modern kitchen featuring a large island with seating for four. A spacious seating area with a blue couch complements the dining space, while a sliding door leads to an outdoor patio. Ample lighting enhances the contemporary design.

Apartment in Rockport

Long Beach Suites: Steps Away From Surf!

Recently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in one of our two bedroom apartment suites. Expertly built with summer visitors in mind. Long Beach Suites is just steps away from Long Beach in Rockport and only ten minutes to Good Harbor. You will be staying one of four similar apartments, photos may not be of exact unit.

KitchenIndoor spacesCondition

A contemporary house is set amidst lush greenery and vibrant flowers, showcasing a large yard. The exterior features large windows and a wraparound balcony on the upper level, while the surrounding garden is filled with various blooming plants.

4.85 out of 5 average rating, 222 reviews

Gloucester Private Contemporary 4 bedrooms

A contemporary private house with large yard in quiet and exclusive goose cove bay neighborhood offers the perfect space for a summer sojourn. Everyone in your group will love being only minutes away from some of the best beaches, activities, history, and food in New England!

Indoor spacesFamilyHeating

Popular amenities for Gloucester family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 165 reviews

The historic carriage house is presented in a charming turquoise color, surrounded by lush greenery and flowering plants. Tall windows provide ample natural light. A spacious yard is visible, framed by a low stone wall and iron fence.

Guesthouse in Rockport

Historic Carriage House | Dog Friendly | Hot Tub

FamilyIndoor spacesBeach

4.95 out of 5 average rating, 183 reviews

A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.

Home in North Andover

Nana-tucket Inn

FamilyKitchenAmenities

Farm stay in North Andover

4.97 out of 5 average rating, 130 reviews

Winery Farmhouse w/ Private Hot Tub & Wine Tasting

FamilyKitchenCheck-in

4.92 out of 5 average rating, 572 reviews

A welcoming sitting area features two comfortable chairs beside a small round table. Natural light floods through large windows, showcasing views of the serene lake. A television is mounted above a decorative fireplace, creating an inviting space for relaxation.

Home in Derry

Little Lake House, the Bungalow

FamilyIndoor spacesView

Superhost

Apartment in Woburn

4.92 out of 5 average rating, 233 reviews

Romantic Getaway w/private Jacuzzi• Fire Pit•

FamilyIndoor spacesOutdoor spaces

4.92 out of 5 average rating, 277 reviews

A spacious living room features a large sectional couch and an accent chair, both positioned on a patterned area rug. A wall-mounted TV is visible, with light streaming through the windows, highlighting the natural wood flooring and airy design.

Home in Derry

Sanctum by the Lake

KitchenIndoor spacesBeach

4.98 out of 5 average rating, 216 reviews

A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

Indoor spacesFamilyView

Guest suite in Kittery Point

Outdoor dining tables are set under large umbrellas, with guests enjoying a waterfront view. Sailboats are anchored in the calm water during sunset, creating a serene coastal atmosphere. The soft colors of the sky reflect on the water, enhancing the picturesque dining experience.

4.95 out of 5 average rating, 376 reviews

Close to Beaches, Portsmouth, Shopping + Hot Tub

KitchenFamilyGrill

Family- and pet-friendly home rentals

Apartment in Manchester-by-the-Sea

4.91 out of 5 average rating, 194 reviews

Private Pool Retreat w/Fire Pit Near Singing Beach

FamilyKitchenHospitality

4.81 out of 5 average rating, 99 reviews

A vibrant sunset casts warm orange and yellow hues across the ocean's surface, reflecting on gentle waves. Silhouetted rocks line the shore, while distant land appears along the horizon, creating a serene coastal scene.

Home in Rockport

Sea Vagabond - Watch the waves, stroll to the sand

Indoor spacesKitchenCondition

Aerial view of the spacious home reveals a wraparound deck with multiple seating areas, including shaded tables beneath umbrellas. The exterior features a light yellow façade complemented by large windows, surrounded by greenery that enhances the property's serene, secluded ambiance.

4.92 out of 5 average rating, 127 reviews

Aerie, 2 king beds, large space, AC, 2 beaches!

FamilyKitchenAmenities

4.99 out of 5 average rating, 159 reviews

A cozy outdoor seating area overlooks the water, featuring two wicker chairs and a matching sofa arranged around a low table. A striped area rug anchors the space. The railing provides an unobstructed view of the rocky coastline and distant shoreline.

Apartment in Rockport

3 Bedroom Apartment with parking on Bearskin Neck

Indoor spacesFamilyBathroom

4.9 out of 5 average rating, 131 reviews

Home in Ipswich

Hillside Ocean View 2BR with Private Beach Access

KitchenFamilyHiking

5.0 out of 5 average rating, 154 reviews

A cozy living room features large windows that invite natural light, accented by a ceiling fan. Comfortable brown leather seating surrounds a dark coffee table, which holds magazines. A light-colored area rug complements the space, while a wall-mounted shelf displays decorative items.

Apartment in Salem

2-Bedroom Ocean View Walk to Beach and Downtown

FamilyIndoor spacesWalkability

4.99 out of 5 average rating, 207 reviews

A deck overlooking the water features a round table surrounded by four chairs, each with turquoise cushions. An umbrella stands in the center of the table, providing shade. A decorative rug with an oceanic design is positioned underneath the table, complementing the serene water views.

Cottage in Eliot

Salty Mermaid Cottage/Boat House

KitchenFamilyAccuracy

4.82 out of 5 average rating, 135 reviews

The exterior of a summer cottage is showcased, with a light grey wooden structure resting on a rocky landscape. Stairs lead up to the entrance, flanked by greenery. A deck with railings is visible on the upper level, complemented by large windows allowing natural light.

Cottage in Rockport

Retreat in the Trees- walk to Cape Hedge Beach

FamilyKitchenHiking

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 163 reviews

Cottage in Marblehead

Pool Is Open! Steps from Harbor + Walk to Old MHD

FamilyIndoor spacesGrill

4.93 out of 5 average rating, 139 reviews

Cottage in Plum Island

Sunset Waterfront Retreat | Private Beach, Pool &

KitchenFamilyLocation

4.95 out of 5 average rating, 100 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

FamilyKitchenTV

Guesthouse in West Roxbury

A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.

4.95 out of 5 average rating, 215 reviews

Country Cottage in the City

KitchenFamilyNearby

4.94 out of 5 average rating, 253 reviews

A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.

Guesthouse in Newton

Charming 2-story private Guesthouse

FamilyIndoor spacesWalkability

4.88 out of 5 average rating, 203 reviews

A cozy living area features a spacious daybed flanked by decorative pillows. Two armchairs are positioned across from a coffee table, enhancing the seating arrangement. A decorative vase adds charm beside the fireplace, while natural light filters through the window, illuminating the wood flooring.

Guest suite in Revere

Amazing studio

Indoor spacesKitchenPool

4.97 out of 5 average rating, 344 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

Private Suite• Pool • Sleeps 4 • Boston • Airport

FamilyKitchenAccess