Family-friendly vacation rentals in Rockport

A cozy living area features a plush couch adorned with a throw blanket, set against a backdrop of exposed wooden beams. Stylish shelving displays decorative items, while natural light floods in through two inviting windows, complementing the warm hardwood flooring.

4.98 out of 5 average rating, 130 reviews

Walk to Shops & Beach at Historic Renovation

Are you dreaming of sun, sand and seafood? Stay at the 1767 Tuck House, where historic charm meets quintessential New England luxury! This is the perfect home for groups. Steps to the beach, shops, restaurants and arts. Home offers the privacy of boutique hotel with modern comforts: plush Casper mattresses, AC, 4K HDTV, laundry, heated floors, quartz counters, new appliances, 3BR, 3 Full Baths, 2 Kitchens, 2 Decks, Private Entries. A true Rockport gem, we promise a special stay.

KitchenFamilyValue

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.

4.99 out of 5 average rating, 175 reviews

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.

FamilyIndoor spacesCleanliness

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.

4.99 out of 5 average rating, 165 reviews

3 Bedroom Apartment with parking on Bearskin Neck

Built in 1822, the Sound House is conveniently located on Bearskin Neck. The upstairs apartment is renovated with brand new oak floors, new bathrooms, and updated living area. The unit features 3 bedrooms and 2 full bathrooms, with laundry as well as 3 parking spaces in the back of the building. The kitchen includes cooking utensils, with an electric grill and butane burner for outdoor cooking on the new deck overlooking Cape Ann. Enjoy Rockport while creating new memories at the Sound House!

FamilyKitchenView

4.93 out of 5 average rating, 180 reviews

Old Harbor

Right on the Old Harbor on Bearskin Neck, a 2 story light, airy apartment just steps from shops, restaurants, and beaches-the top two floors of the building. Amazing views from large bay windows, enormous deck complete with table and chairs. Two beds (1 Queen, 1 Full) + a full-size pullout sofa. One on-site parking space for a small to mid-size car. Mini-split A/C units on each floor. Bring your kayak or paddleboard, step down 3 stairs and you are in the water! Have a good swim!

Indoor spacesKitchenAccess

4.99 out of 5 average rating, 174 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 spacesFamilyLaundry

5.0 out of 5 average rating, 110 reviews

A charming three-story house features a light yellow exterior with large windows and a pitched roof. A welcoming front porch offers a mix of outdoor seating. Lush greenery and trees surround the property, creating a serene atmosphere.

Condo in Rockport

Rockport Getaway near ocean, music hall & downtown

This private, newly-renovated, well-appointed entire two-bedroom garden apartment comfortably sleeps four with full kitchen, bathroom, washer/dryer, central A/C. Desirably located, just steps to Rockport Harbor, restaurants, shopping, Shalin Liu Performance Center and short walk to beaches. Free onsite parking for two cars. Exclusive side yard use with patio, outdoor furniture and table. Bright & airy, it's a quiet, restorative getaway. Available for longer winter rental too.

KitchenFamilyCheckout

A bright living area features large windows with views of a garden and ample natural light. A comfortable dark sofa and a plush chair are arranged around a glass coffee table on a colorful area rug. A wooden dresser and a small dining table add warmth to the space.

4.97 out of 5 average rating, 376 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.

Indoor spacesKitchenBreakfast

4.98 out of 5 average rating, 765 reviews

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

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.

Indoor spacesFamilyLaundry

A bright entryway features a glass door that opens to a view of the water. Sunlight filters through, illuminating a welcoming space. An umbrella stand and a wicker basket are visible near the entrance, adding practicality to the design.

4.99 out of 5 average rating, 116 reviews

Downtown Cottage-DeckツParkingツOceanツBeachesツShopsツ

Discover coastal charm at this historic Rockport, MA gem! Breathtaking seaside views, beaches, cafes, art shops, and the Shalin Liu Performance Center nearby. Walk to iconic Motif #1, kayak, hike, or unwind at the beach. Explore nearby Salem, MA, known for its witch trials history, or take a day trip to bustling Boston, just a short drive or train ride away. Experience the best of New England coastal living. Book now!

KitchenIndoor spacesCondition

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.

4.93 out of 5 average rating, 105 reviews

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

KitchenFamilyBathroom

The entryway features a bright, welcoming atmosphere with white paneling and natural wood accents. A staircase ascends to the upper level, while a door with a frosted window leads outside. A round mirror hangs above a striped rug, enhancing the space's inviting feel.

4.82 out of 5 average rating, 149 reviews

Ocean View unit with Private Roofdeck in Rockport

Enjoy beautiful ocean views from Bearskin Neck! This cute and cozy 1-2 bedroom unit has been completely renovated. Nice bright colors and sea decor thoughout. Downtown Bearskin Neck location offers beaches, harbors, kayaking, ocean breezes and fresh seafood - all steps from your door! Unit has private roofdeck with astonishing views. Enjoy relaxing on the roofdeck with a glass of wine while watching the sunset!

FamilyIndoor spacesGetting around

A serene waterfront view captures a white boat moored near a dock. Surrounding structures, including a notable red building and other historic homes, reflect a charming coastal atmosphere. Calm waters mirror the scenery under a clear sky, emphasizing the peaceful surroundings.

4.91 out of 5 average rating, 187 reviews

Directly on the water! Private parking!

Location location location! In the heart of Rockport's Bearskin Neck area. Steps away from restaurants, shopping, and art galleries, yet tucked away on a quiet side street. 5 minute walk to the beach. Recently remodeled and decorated in a nautical theme. This spacious 330 sq ft studio looks onto Rockport Harbor and historic Motif #1 (the famous red fish shack). INCLUDES PRIVATE PARKING SPACE steps away.

FamilyIndoor spacesCleanliness

Popular amenities for Rockport 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, 184 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

KitchenFamilyBiking

Farm stay in North Andover

Winery Farmhouse w/ Private Hot Tub & Wine Tasting

KitchenIndoor spacesLaundry

4.97 out of 5 average rating, 135 reviews

Superhost

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

KitchenFamilyGetting around

4.91 out of 5 average rating, 242 reviews

4.98 out of 5 average rating, 221 reviews

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

Indoor spacesFamilyHot tub

4.96 out of 5 average rating, 285 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.

KitchenIndoor spacesTV

4.78 out of 5 average rating, 359 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!

KitchenIndoor spacesLong stay

An aerial view showcases a large three-story house with a classic New England design, surrounded by lush greenery. The property is situated near the coastline with views of the ocean, featuring manicured lawns and pathways leading to outdoor living spaces.

4.98 out of 5 average rating, 58 reviews

Classic New England: Big Family Home; Spas|Garden

FamilyKitchenQuiet

Guest suite in Marblehead

Headers’ Haven

KitchenFamilyPool

5.0 out of 5 average rating, 88 reviews

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 501 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

FamilyKitchenCheck-in

4.83 out of 5 average rating, 138 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

KitchenFamilyHospitality

The exterior of the hilltop unit is shown, featuring a brown wooden facade and white trim. A bright blue door stands out, complementing the landscaped yard with a mix of grass and stone elements. Trees frame the space, creating a serene outdoor setting.

4.89 out of 5 average rating, 214 reviews

Sweet short term rental in Rockport

FamilyIndoor spacesParking

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.

4.81 out of 5 average rating, 101 reviews

Sea Vagabond - Watch the waves, stroll to the sand

FamilyKitchenValue

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, 114 reviews

Ocean views! Welcome to Sea Breeze! Winter rates!

FamilyIndoor spacesHospitality

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, 128 reviews

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

FamilyIndoor spacesPets

4.93 out of 5 average rating, 193 reviews

Waterfront Rocky Neck Cottage | Gloucester Harbor

KitchenFamilyParks

An outdoor deck features wooden flooring and comfortable seating arrangements, including a central coffee table. Potted red flowers add a touch of color to the space. Warm light fixtures hang above, enhancing the inviting feel of the area.

4.98 out of 5 average rating, 104 reviews

Walk2DNTN•Beach•Beauport•Boat Island•Close2Salem

Indoor spacesKitchenBreakfast

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 167 reviews

Cottage in Marblehead

Pool Is Open in Sept! Steps from Harbor + Old Town

FamilyIndoor spacesBiking

4.96 out of 5 average rating, 116 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

KitchenFamilyHospitality

4.87 out of 5 average rating, 209 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

4.93 out of 5 average rating, 141 reviews

Cottage in Plum Island

Sunset Waterfront Retreat | Private Beach, Pool &

Indoor spacesKitchenLocation

4.94 out of 5 average rating, 256 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 spacesDecor

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.

Beautiful Beach Studio

KitchenFamilyAmenities

4.76 out of 5 average rating, 134 reviews