Family-friendly holiday rentals in Gloucester

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

KitchenIndoor spacesValue

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.

FamilyKitchenView

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.

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 spacesFamilyBarbecue

4.92 out of 5 average rating, 251 reviews

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

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2026! 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

Indoor spacesFamilyCondition

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.

Indoor spacesFamilyLocation

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.

Indoor spacesKitchenAir conditioning

4.99 out of 5 average rating, 161 reviews

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.

Condo in Gloucester

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.

KitchenFamilySleep quality

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.

Indoor spacesFamilyWalkability

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 spacesFamilyHospitality

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.

Indoor spacesFamilyTV

4.96 out of 5 average rating, 226 reviews

Loft in Gloucester

Downtown, Shops, Beach, Deck, Close to Salem

Charming Downtown Gloucester Loft 🏙️🌊 Escape to this stylish and spacious loft at 278 Main St, Unit B, Gloucester, MA 01930, located in the heart of downtown Gloucester. Perfect for couples, friends, or small families, you’ll be just steps from restaurants, boutique shops, and the scenic Good Harbor Beach—the ideal blend of city and coastal charm. 🛍️☀️

Indoor spacesKitchenOutdoor spaces

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!

KitchenFamilyView

Popular amenities for Gloucester family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 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

Indoor spacesFamilyQuiet

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

FamilyIndoor spacesAmenities

Superhost

Apartment in Woburn

4.92 out of 5 average rating, 233 reviews

Romantic Getaway w/private Jacuzzi• Fire Pit•

KitchenFamilyComfort

4.92 out of 5 average rating, 140 reviews

A modern kitchen is showcased, featuring gray cabinetry and a large island with seating for four. Stainless-steel appliances are integrated seamlessly, while light reflects off the marble countertops. A dining area is visible in the background, with natural light filtering through a window.

Condo in Brighton

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

KitchenIndoor spacesAccuracy

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 spacesBathroom

4.96 out of 5 average rating, 280 reviews

A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.

Apartment in Winthrop

Oceanfront Pool. Close to Boston. Free Parking.

Indoor spacesFamilyBeach

Superhost

The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.

Farm stay in North Andover

4.93 out of 5 average rating, 301 reviews

Winery Studio w/ Private Hot Tub & Wine Tasting

KitchenFamilyBeach

Guest suite in Marblehead

5 out of 5 average rating, 81 reviews

Headers’ Haven

FamilyKitchenGetting around

Family- and pet-friendly home rentals

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

FamilyIndoor spacesHeating

4.94 out of 5 average rating, 105 reviews

Condo in Swampscott

Ocean View Coastal Retreat | Walk to Beach | Salem

FamilyIndoor spacesComfort

5 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

KitchenIndoor spacesAmenities

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

FamilyIndoor spacesPets

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

Indoor spacesFamilyLayout

4.9 out of 5 average rating, 131 reviews

Home in Ipswich

Hillside Ocean View 2BR with Private Beach Access

FamilyIndoor spacesLayout

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!

FamilyIndoor spacesTV

A spacious private deck overlooks the tidal Annisquam River, featuring comfortable outdoor seating with blue cushions. A small table is placed beside the seating area. String lights illuminate the space, enhancing the inviting atmosphere for relaxation while enjoying scenic water views.

4.91 out of 5 average rating, 47 reviews

PVT Waterfront Deck|Firepit|Workspace|Free Parking

KitchenIndoor spacesCheckout

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 156 reviews

A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.

Apartment in Brighton

The Murthy : Bright • Spotless • W/D

Indoor spacesKitchenLaundry

4.97 out of 5 average rating, 118 reviews

The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.

Home in Weston

Spacious vacation unit in premium suburban town

KitchenFamilyWalkability

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

KitchenFamilyAccess

Apartment in Hampton Beach

A studio apartment features a spacious bed adorned with a patterned quilt in vibrant colors. A dining area with a table and chairs is positioned nearby. Light enters through large windows, and a flat-screen TV is mounted on the wall for convenience.

4.76 out of 5 average rating, 134 reviews

Beautiful Beach Studio

KitchenIndoor spacesQuiet

4.97 out of 5 average rating, 442 reviews

A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.

Apartment in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

FamilyIndoor spacesAir conditioning

4.93 out of 5 average rating, 139 reviews

Cottage in Plum Island

Sunset Waterfront Retreat | Private Beach, Pool &

KitchenIndoor spacesComfort

4.99 out of 5 average rating, 163 reviews

Cottage in Marblehead

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

FamilyKitchenParks