Family-friendly holiday rentals in Gloucester

4.96 out of 5 average rating, 309 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

FamilyKitchenCheck-in

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 spacesBathroom

4.93 out of 5 average rating, 190 reviews

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

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.

KitchenFamilyAmenities

5.0 out of 5 average rating, 3 reviews

Apartment in Gloucester

Stunning Ocean-View Retreat, Magnolia Beach

Escape to this luxury coastal retreat home overlooking the Atlantic ocean. Stunning newly renovated 2-bedroom, 2-bathroom apartment, offers 1,500 sq feet of bright and sunny living space. Free off street parking for two cars included. Bedrooms both have king size beds. Fully equipped kitchen with high-end appliances. Cable TV & WiFi included. Washer and dryer in unit. Located near Magnolia beach, Coolidge Reservation, Hammond Castle, Stage Fort Park. Beauport Hotel, downtown Gloucester.

Indoor spacesLocationView

4.92 out of 5 average rating, 250 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

KitchenIndoor spacesLayout

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

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, kitchen, queen sized bed with en-suite bathroom and sun room that converts to an extra sleeping space perfect for kids. A short walk to the train for day trips to Salem, Gloucester, and Boston!

Indoor spacesFamilyBarbecue

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.

KitchenIndoor spacesLayout

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.

KitchenIndoor spacesGetting around

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 spacesKitchenNearby

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 spacesFamilyPets

5.0 out of 5 average rating, 198 reviews

An aerial view displays the proximity of the condo to two beaches in Cape Ann. The map highlights a central location marked by a dot, surrounded by greenery and coastal features, with the ocean visible nearby.

Townhouse in Gloucester

Between 2 Beaches

This 3-level, 3-bedroom, 2.5-bathroom, recently renovated, beach-themed condo is fully stocked and features 2 unique outdoor spaces. Located right between 2 of Cape Ann’s most amazing beaches — Good Harbor Beach in Gloucester and Long Beach in Rockport — Take your pick — no need to drive or pay for beach parking, as both beaches are just a short walk away!

KitchenIndoor spacesValue

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. 🛍️☀️

KitchenFamilyBiking

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

KitchenFamilyDecor

Farm stay in North Andover

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.

4.93 out of 5 average rating, 301 reviews

Winery Studio w/ Private Hot Tub & Wine Tasting

Indoor spacesKitchenValue

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

KitchenFamilyValue

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

KitchenIndoor spacesNearby

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 spacesLaundry

4.92 out of 5 average rating, 233 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

KitchenFamilyQuiet

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 spacesFamilyGetting around

4.78 out of 5 average rating, 358 reviews

The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.

Apartment in Roxbury

Modern, Spacious 1BR for 4 - Easy Marathon Access!

Indoor spacesFamilyLaundry

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 110 reviews

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.

Home in Gloucester

Ocean views! Welcome to Sea Breeze! Winter rates!

Indoor spacesFamilyBeach

Apartment in Manchester-by-the-Sea

4.91 out of 5 average rating, 194 reviews

Private Pool Retreat w/Fire Pit Near Singing Beach

Indoor spacesKitchenOutdoor spaces

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

FamilyIndoor spacesView

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

KitchenFamilyGetting around

4.92 out of 5 average rating, 127 reviews

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.

Home in Gloucester

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

Indoor spacesKitchenCheckout

4.9 out of 5 average rating, 131 reviews

Home in Ipswich

Hillside Ocean View 2BR with Private Beach Access

KitchenIndoor spacesParking

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 spacesCheckout

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 spacesFamilyBarbecue

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 139 reviews

Cottage in Plum Island

Sunset Waterfront Retreat | Private Beach, Pool &

KitchenFamilyBarbecue

4.99 out of 5 average rating, 163 reviews

Cottage in Marblehead

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

Indoor spacesFamilyCleanliness

4.95 out of 5 average rating, 100 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

KitchenFamilyNearby

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

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

FamilyIndoor spacesOutdoor spaces

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

FamilyIndoor spacesSolo travel

4.94 out of 5 average rating, 252 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 spacesAccuracy