Family-friendly vacation rentals in Rockport

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, 173 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.

KitchenFamilyDecor

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, 162 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!

KitchenIndoor spacesBeach

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 spacesFamilyGetting around

4.99 out of 5 average rating, 139 reviews

A view of a waterfront building is framed by leafy tree branches. A staircase leads to a second-floor entrance. Brightly colored kayaks are lined up along the calm water's edge, with a wooden dock visible in the background.

Condo in Rockport

Harbor Place - Airy hideaway over Rockport Harbor

Enjoy stunning views of Rockport Harbor and the Atlantic from Harbor Place, a breezy, quiet open-floorplan bnb on Tuna Wharf, steps from the galleries, shops and restaurants of bustling Bearskin Neck. You'll be within easy strolling distance of several beaches, the train station, the Shalin Liu Performance Center, kayak rentals, walking paths, parks and boat tours. Relax and enjoy the view, eat in or out, lounge on our private beach! Access to Harbor Place is via staircase.

Indoor spacesFamilyGetting around

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.

Indoor spacesKitchenCleanliness

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, 373 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.

FamilyIndoor spacesAccuracy

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

"The Sea Vagabond House is an expanded 1932 summer cottage, with spectacular views of the ocean waves, with the tidal Saratoga Creek offering a mesmerizing and changing scenes from inside and outside this charming vacation home. The home sleeps eight comfortably in beds. Each level offers a full bathroom with a bathtub/shower. There are plenty of bath towels and beach towels for each guest. "Comfortable, clean and close to the beach, we will return."

KitchenIndoor spacesGetting around

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

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.

KitchenIndoor spacesHiking

4.98 out of 5 average rating, 763 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.

FamilyIndoor spacesLaundry

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, 115 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 spacesTV

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

Indoor spacesFamilyBeach

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!

Indoor spacesFamilyValue

Popular amenities for Rockport family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 171 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 spacesBackyard

4.95 out of 5 average rating, 185 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

KitchenIndoor spacesHeating

Farm stay in North Andover

4.97 out of 5 average rating, 132 reviews

Winery Farmhouse w/ Private Hot Tub & Wine Tasting

Indoor spacesFamilyBathroom

4.98 out of 5 average rating, 221 reviews

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

FamilyIndoor spacesSleep quality

4.92 out of 5 average rating, 237 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

FamilyKitchenNearby

4.96 out of 5 average rating, 284 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.

FamilyIndoor spacesHot tub

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 spacesBathroom

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

FamilyKitchenAccess

Family- and pet-friendly home rentals

4.82 out of 5 average rating, 137 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 spacesFamilyPets

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 spacesCheckout

4.98 out of 5 average rating, 112 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!

FamilyKitchenLong stay

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!

FamilyIndoor spacesCheckout

4.93 out of 5 average rating, 192 reviews

Home in Gloucester

Waterfront Rocky Neck Cottage | Gloucester Harbor

KitchenFamilyAmenities

4.96 out of 5 average rating, 205 reviews

Condo in Gloucester

KeyWest Vibe, PrivatePatio, Close2Salem, WalkDWNTN

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 265 reviews

The living area features a mix of comfortable seating, including a floral-patterned sofa and a plaid armchair. A round coffee table sits atop a light blue area rug, and large windows allow natural light to fill the space, enhancing the cozy ambiance.

Condo in Marblehead

Harbor View Suite

FamilyKitchenBathroom

4.94 out of 5 average rating, 124 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!

Indoor spacesKitchenBathroom

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

Indoor spacesKitchenLaundry

Apartment in Manchester-by-the-Sea

4.91 out of 5 average rating, 200 reviews

Private Pool Retreat w/Fire Pit Near Singing Beach

KitchenIndoor spacesLocation

4.95 out of 5 average rating, 111 reviews

Apartment in Everett

Curated Designer Retreat • Pool • Gym • Dining

FamilyKitchenLaundry

4.88 out of 5 average rating, 206 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 spacesFamilyDecor

4.93 out of 5 average rating, 140 reviews

Cottage in Plum Island

Sunset Waterfront Retreat | Private Beach, Pool &

Indoor spacesKitchenPool

4.94 out of 5 average rating, 255 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

KitchenFamilyView

Superhost

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

4.95 out of 5 average rating, 161 reviews

The Murthy : Bright • Spotless • W/D

FamilyKitchenTV