Family-friendly holiday rentals in Eastham

4.89 out of 5 average rating, 238 reviews

Guest suite in Orleans

Charming Old Cape Cod Waterfront

Indulge in relaxation and leisure at Snowtop on the Town Cove. The charming retreat features a private entrance, a spacious bedroom with a king size bed, a full bath, and a sunlit living room with a dining table overlooking picturesque Town Cove. The view in the photo is your front yard. Guests often enjoy sitting outside to watch boats drift by and the sky change color to a sunset. Nestled on a quiet road, Snowtop is 3 miles from beautiful Nauset Beach and 2 miles from the center of Orleans.

Indoor spacesFamilyValue

An open living space showcases a comfortable blue sofa and a large wooden dining table. Natural light floods the area through sliding doors, leading to an outdoor patio. Neutral tones and wooden accents create a cohesive and inviting environment for relaxation and gatherings.

4.99 out of 5 average rating, 110 reviews

Spacious beautiful fully renovated Cape Cod escape

Beautifully furnished,fully renovated 4BD, 3BT duplex in Fantastic location.Spacious yard. At the end of a cul-de-sac.Within minutes of Beaches, Trails, Great Pond and Wiley Park. The open living space invites gatherings of family and friends. Cape Cod escape.Modern bathrooms, fully equipped kitchen with new appliances. Great outdoor space, patio, big tables- inside and outside, grill, plenty of parking, A/C window units, W/D. Sleeps up to 10. Linens, beach towels/chairs & an umbrella provided.

KitchenIndoor spacesOutdoor spaces

4.9 out of 5 average rating, 100 reviews

A spacious outdoor patio area features a dining table with chairs, surrounded by lounge chairs. Vibrant red Adirondack chairs are positioned nearby, and various potted plants add a touch of greenery. The setting is bordered by trees and grass, offering a peaceful atmosphere.

Cottage in North Eastham

Modern, Clean Cottage • Walk to Campground Beach

Just 900 steps to Cape Cod Bay, this Bay Road property offers two ajacent quiet cottage units situated on 3/4 of an acre in the Campground Beach area of North Eastham. This charming cottage area provides a perfect setting for your memorable vacation. The National Seashore beaches, the Audubon, and cape cod rail trail (bike path) are easily accessible. Other activities such as restaurants, mini golf, bike rentals are nearby. The property is newly renovated, with new kitchen, bath and flooring.

Indoor spacesKitchenHeating

A contemporary cape-style home is framed by lush greenery and tall trees, set back from a sandy path leading to the entrance. The home features a charming front porch with large windows, offering a welcoming presence amidst the tranquil outdoor surroundings.

4.79 out of 5 average rating, 166 reviews

Contemporary Cape, Marsh/Bird Sanctuary views, AC!

Unwind in paradise! This stunning property offers the best of both worlds: refreshing breezes from the marsh through open windows and doors, and newly installed Air Conditioning for rare, scorching days. Wake up to sunrises, a symphony of birds, the endangered Osprey, Great Blue Heron, and Egrets outside your window. Audubon is across the marsh. At night, owls, moonrise, and stars!! A bright, airy oasis on a quiet cul-de-sac, minutes from the beach, shopping, and scenic bike/rail trail.

FamilyKitchenAir conditioning

A serene beach scene captures a gentle stream flowing through soft sand, leading to the ocean. The clear blue sky reflects sunlight across the water's surface, highlighting the expansive shoreline. Minimal vegetation and distant structures provide a sense of tranquility to the landscape.

5.0 out of 5 average rating, 51 reviews

5 Min Walk to Bay Beach! Large, Newly Renovated!

A quiet 5-min WALK to Cole Road beach, a 1/2 mile to the Cape Cod Rail Trail and Wiley Pond. Short 7 min. drive to Coast Guard Beach, and 30 min. to Provincetown. Enjoy a quiet, bayside beach vacation in this spacious home, newly renovated! Location is perfect for vacationers looking to relax at the beach and/or be adventurous. Enjoy stunning sunsets every night and relax in this comfortable and roomy home that is peacefully quiet and has everything you need. Sat. to Sat bookings ONLY please!

KitchenIndoor spacesSleep quality

5.0 out of 5 average rating, 18 reviews

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

KitchenIndoor spacesBeach

4.92 out of 5 average rating, 214 reviews

The kitchen area features a wooden pitched ceiling and a functional layout. A farmhouse sink is paired with stainless steel appliances and cooking essentials. Two stools are positioned at a counter, with a small vase of flowers adding a touch of nature. Glass doors offer views to an outdoor deck.

Home in Wellfleet

Wellfleet Woods Escape

Open kitchen + living + dining, w/ a wooden pitched ceiling and two sliders overlooking the deck, backyard +marsh. Functional kitchen with Farm sink, DW, cooking and pantry essentials. Two comfortable bedrooms with window AC's, new mattresses, and blackout curtains. Bathroom w/ tub/shower + plenty of towels for beach or house use. Outdoor shower is great in warmer months! Enjoy this quiet, tucked away Wellfleet spot with lots of walking trails and beautiful sunset views just down the road.

FamilyIndoor spacesComfort

4.97 out of 5 average rating, 203 reviews

A charming cottage is surrounded by a grassy yard, featuring a set of four blue Adirondack chairs arranged around a small glass table. A gas grill is situated nearby, and a tree provides dappled shade to the area.

Guest house in Wellfleet

Abundant Blessings Cottage – Wellfleet

Couple/family fun all year in a charming, private Cape Cod cottage w/ screened in porch, patio & outdoor shower (in Nov/Dec/Jan becomes a Gingerbread cottage). Inside: open living space w/ queen bed & sitting space. Ladder leads to a short height sleeping loft w/ 2 twin beds. Full bathroom w/ indoor shower. Kitchenette- see description below. We supply tea, local coffee, spices, condiments, gas grill, ice chests, beach towels & chairs. To sleep up to 8, also rent our Upper Room on Airbnb.

Indoor spacesFamilyTV

4.95 out of 5 average rating, 153 reviews

A private balcony features a small white table and two wine glasses, set among comfortable lounge chairs. Lush greenery surrounds the area, creating a serene and secluded outdoor space, perfect for relaxation.

Guest suite in Eastham

Cape Cod Heaven

Private one bedroom with full bath and balcony overlooking garden and a peek at the bay. Great location less than a mile from beautiful First Encounter Beach, a wonderful bay beach, and five minute walk to freshwater pond with sandy beach. Ocean beaches and bike trail close by. Bring your bikes or kayaks, or rent them, and enjoy all the Cape has to offer. Great for singles, couples, small families. Has a small refrigerator, microwave and Keurig. There is not a kitchen.

KitchenIndoor spacesWifi

A classic Cape house with a gabled roof showcases a welcoming facade. The exterior features red shutters, multiple windows, and landscaped gardens with flowering plants. A gravel driveway leads up to the entrance, which is framed by decorative shrubs, contributing to a peaceful, inviting setting.

4.99 out of 5 average rating, 147 reviews

Bayside Bliss

Classic Cape house on a quiet road just steps from the Cape Cod Rail Trail bike path and 1/2 mile from a sparkling pond. Cape Cod bay is 1.3 miles away. Woods, wind and sun await you! Spacious 4 bedroom, 2 bath home with beautiful sun porch...4 NIGHT MINIMUM. Kindly introduce yourself in your inquiry - we appreciate hearing details about your group and your reason for visiting Cape Cod. There is a 7 NIGHT SUNDAY - SUNDAY MINIMUM from July 5 - August 16.

Indoor spacesKitchenGrill

A charming exterior of the Carriage House features weathered shingle siding and a cupola on the roof. Surrounded by landscaped gardens, the entrance showcases a well-kept pathway and a mix of greenery and blooming flowers, creating a welcoming ambiance.

4.96 out of 5 average rating, 207 reviews

The Sea Captain's Carriage House

The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.

Indoor spacesKitchenNearby

4.95 out of 5 average rating, 314 reviews

A charming cottage is nestled on a hillside, surrounded by lush greenery. The exterior features a light wood facade and a welcoming front porch with seating. The landscaped yard is manicured, offering a natural setting that blends harmoniously with the surrounding environment.

Cottage in Wellfleet

Hillside Cottage

A one-bedroom cottage that sleeps 4, nestled into the hillside at the top of the wetland. Great for birding! Located on a beautifully landscaped property walking distance to Lecount Hollow Beach. The bedroom has a queen bed and there is a queen sleep sofa in the finished basement. There is also a studio apartment available on the premises that sleeps two. The listing name is "Comfortable Studio Apartment".(Pets are allowed in the studio appartment)

Indoor spacesKitchenCheck-in

Popular amenities for Eastham 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, 320 reviews

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

Home in Chatham

Slate House - a modern waterfront getaway

Indoor spacesKitchenHospitality

4.96 out of 5 average rating, 168 reviews

Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.

Cottage in South Dennis

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Indoor spacesFamilyBiking

4.98 out of 5 average rating, 384 reviews

Tiny home in Wellfleet

Writer’s Cabin • On-Site Hot Tub & Wood-fire Sauna

FamilyKitchenHiking

4.97 out of 5 average rating, 236 reviews

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

Home in Dennis Port

Lakefront House/Private Dock/Year Round Hot Tub/AC

FamilyKitchenCheckout

5.0 out of 5 average rating, 102 reviews

An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.

Apartment in Brewster

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Indoor spacesKitchenBiking

4.83 out of 5 average rating, 105 reviews

The beachfront property is showcased against a vibrant sunset sky, with gentle waves lapping the sandy shore. Steps built into the rocky landscape lead down to the beach, while coastal homes are visible in the background, creating a serene and inviting setting.

Home in Dennis Port

Gorgeous Modern Ocean-Front Cottage With Hot Tub

Indoor spacesKitchenAmenities

4.86 out of 5 average rating, 113 reviews

An outdoor space features a cozy seating area with blue cushions surrounding a fire table. A dining table is set nearby, accompanied by a grill and outdoor kitchen. String lights provide subtle illumination, enhancing the space for gatherings. A television is mounted on the wall.

Home in East Dennis

Speakeasy Bar • Hot Tub • PetsOK• Close2Mayflower

KitchenFamilyHot tub

4.92 out of 5 average rating, 319 reviews

The cottage, surrounded by mature landscaping, is located near a private beach. A sandy expanse is visible in the background, highlighting the close proximity to the shore. Nearby structures exhibit a rustic charm, contributing to the serene beach environment.

Cottage in Sandwich

Hideout at Water's Edge, 131 North Shore Blvd, #4

KitchenIndoor spacesAmenities

Family- and pet-friendly home rentals

5.0 out of 5 average rating, 104 reviews

A charming garden studio is nestled under a canopy of pink flowering trees, surrounded by lush green grass. A ladder leans against one of the trees, enhancing the natural landscape, while the studio's large windows reflect the vibrant colors of spring.

Guest house in Wellfleet

Marshfront Retreat | EV Charger | Private Deck

KitchenIndoor spacesLocation

4.98 out of 5 average rating, 132 reviews

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich

Spacious cottage beach Wychmere < 4 min Central AC

Indoor spacesKitchenAir conditioning

A charming exterior of a single-story home is framed by a well-maintained lawn and trees. A gravel pathway leads to a screened porch, where rocking chairs are visible. The attractive shingle siding is complemented by a brick chimney, and a small blue shed is present in the background.

4.92 out of 5 average rating, 13 reviews

Brook House on the Bay Side

KitchenIndoor spacesGetting around

A charming cottage with a shingle exterior is set among tall trees. A covered porch with a railing invites relaxation. Large front windows provide ample natural light, while stone steps lead to the entrance. Surrounding landscaping features a mixture of gravel and greenery.

4.92 out of 5 average rating, 36 reviews

Dog friendly, close to bay beaches & bike path

Indoor spacesFamilyCondition

5.0 out of 5 average rating, 12 reviews

Game Room- Movie Projector Room- Fire Pit

KitchenFamilyHospitality

4.96 out of 5 average rating, 68 reviews

A decorative sign features the text '1130 Time & Tides' in elegant script. The sign is set against a wooden shingle backdrop, highlighting its nautical theme with an image of a sailboat and waves, conveying a connection to the coastal location.

Cottage in North Eastham

Time and Tides on Cape Cod Bay

KitchenFamilyLayout

Superhost

Cottage in North Eastham

5.0 out of 5 average rating, 3 reviews

85 Boreen

HospitalityLocationBeach

4.82 out of 5 average rating, 38 reviews

A spacious cedar deck is furnished with a picnic table and two wooden lounge chairs, surrounded by greenery. The cottage features a screened-in porch with large windows, allowing natural light to illuminate the interior while blending outdoor and indoor living.

Cottage in Eastham

1940 Cottage Studio/Loft Style Stunner! Dogs ok!

KitchenIndoor spacesComfort

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 178 reviews

A heated indoor pool is framed by sleek gray walls and illuminated with recessed lighting. Large sliding glass doors offer a view of the outdoor patio. Colorful pool floats and equipment are neatly arranged nearby, providing options for leisure activities.

Home in Plymouth

Seaview Summit | Ocean Views, Indoor Pool, Beach

Indoor spacesFamilyGetting around

4.87 out of 5 average rating, 123 reviews

The exterior of the Cape Cod cottage is shown, featuring a light-colored siding and a unique turret-like structure. Lush green landscaping surrounds the home, which is set back from a gently curved pathway. Tall trees provide natural shade in the area.

Townhouse in Brewster

Ocean Edge Cape House with Beach, Pool, and AC

KitchenFamilyTV

4.87 out of 5 average rating, 67 reviews

A charming cottage exterior is showcased, featuring natural wood shingles and red shutters. A bright orange door provides a welcoming entrance. Lush green leaves frame the image, highlighting the serene surroundings of the property against a clear sky.

Cottage in Wellfleet

Wellfleet~Beautiful One Day Perfect The Next

Indoor spacesFamilyCheck-in

4.98 out of 5 average rating, 53 reviews

Home in Brewster

Modern Cape, Private Heated Pool, Beach, Golf

Indoor spacesKitchenQuiet

4.91 out of 5 average rating, 23 reviews

Apartment in Brewster

Bright Cape Condo in Ocean Edge

Indoor spacesFamilyView

Superhost

A distinctive A-frame cottage is situated among tall trees, surrounded by natural greenery. The entrance features a wooden deck with a picnic table and two chairs, inviting relaxation in the outdoors. Clear skies provide ample sunlight, enhancing the cottage's inviting atmosphere.

Cottage in Wellfleet

4.91 out of 5 average rating, 11 reviews

The Cottages at Even'tide Resort - Seagull

FamilyIndoor spacesQuiet

4.86 out of 5 average rating, 44 reviews

A light-filled living area features a beige sofa and a matching loveseat, accented by navy and white decorative pillows. A round wooden coffee table sits in the center, surrounded by a patterned area rug. Sliding glass doors provide access to the outdoor space.

Townhouse in Brewster

Ocean Edge Townhouse/Pool Access

KitchenIndoor spacesPets