Family-friendly holiday rentals in Harwich

4.83 out of 5 average rating, 127 reviews

2BR Directly on Pleasant Beach – 30 Steps to Ocean

You are not near the beach- You are on it! Only 30 steps from your door to the ocean! Fall asleep to waves. This is a true beachfront cottage located directly on Pleasant Beach. Drink your morning coffee watching the tide roll in. This adorable cottage is reflective of old Cape Cod and is part of a direct beachfront triplex property in the heart of Cape Cod with panoramic views of Pleasant Beach. You'll never feel like you need to leave the cottage but it is close to the quaint Harwich village.

KitchenFamilyView

4.87 out of 5 average rating, 242 reviews

A wooden dock extends into a serene freshwater pond, surrounded by lush green foliage. The calm water reflects the clear blue sky and distant tree line, creating a tranquil setting for relaxation and outdoor activities.

Home in Brewster

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

FamilyIndoor spacesNearby

A charming colonial home is framed by vibrant yellow blooms. The front porch features a welcoming entrance with a dark door and white trim, flanked by two large windows. Lush greenery surrounds the property, creating a serene atmosphere.

5.0 out of 5 average rating, 246 reviews

Harwich Retreat on Cape Cod - Relax or explore!

Enjoy the tranquility of Cape Cod in all seasons. Short walk to the beach. Sleeps 8. Comfortable colonial with open living, dining & kitchen floor plan. 1st floor: full bath with large custom shower & laundry, 4th bedroom/study with picture window overlooking beautiful English-styled gardens. Dining room opens through french doors to a small deck & extensive outdoor living areas with pond, fire pit & outdoor shower. 2nd floor: 3 bedrooms (King, Queen & Twin), luxurious bath w/ deep soaker tub.

KitchenIndoor spacesParking

4.96 out of 5 average rating, 165 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*

Welcome to the Bayside Retreat! Enjoy the real Cape Cod in this Quintessential Beach Rental Featuring: Private hot tub, outdoor patio & sofa set in a peaceful backyard 🕊️ 2️⃣ Kayaks- Outdoor Shower- Gas Grill 🔥 Indoor Gas Fireplace ❄️ Mini Splits ✔️Games ✔️Washer/Dryer 📺 55” Sony TV w/ Apps & DirectTV 🛋️ Comfy Furnishings➕Stocked Kitchen 🛁New Bathroom 🕊️Relax out back in peace & privacy or go explore! 📍 Centrally located ❌NO FEES ⛱️ Year Round Beach Vacation ➡️Bayside_Retreat_Capecod

Indoor spacesKitchenAir conditioning

The outdoor deck is shown with a dining area featuring a large table surrounded by black wicker chairs. An umbrella provides shade, while lush grass and garden elements frame the space. The house's light blue siding and chimney are visible, complementing the serene backyard setting.

5.0 out of 5 average rating, 68 reviews

Beautiful, Family Friendly, under 1 mile to Beach

Immaculate and beautifully renovated home set on a quiet Harwich Port cul-de-sac. Located within minutes from Red River beach and quintessential downtown Harwich Port, and close to the Chatham line. Fully renovated with warm and tasteful design touches throughout, such as Serena & Lily seating. Sleeps up to 8 comfortably. Enjoy two separate living areas, a 70-inch TV, cedar outdoor shower, bedroom ACs, a fitness space, a large deck space with ample seating, and a great back yard green space.

FamilyIndoor spacesNearby

4.97 out of 5 average rating, 296 reviews

Home in Dennis Port

Pet Friendly - Walk to Downtown Dennis Port!

Newly renovated - cozy, clean and bright! PET FRIENDLY! (PRE APPROVAL required) All amenities provided for an enjoyable and relaxing family vacation or quick get-a-way! Three car driveway and private outdoor shower. Five minute walk to Dennis Port Main Street shopping, restaurants, yoga, Pet Salon, and Town playground. South Side Beaches and Ponds just 1 mile away as well as Cape Cod Bike Trail minutes away! Pet friendly beaches in Dennis after Labor Day and before Memorial Day weekends.

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 661 reviews

A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.

Guest suite in Harwich

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Eleven year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

KitchenIndoor spacesAccuracy

A charming single-story home is presented with light grey shingles and dark blue shutters. A paved pathway leads to the front door, framed by manicured green lawns and landscaped flower beds. Trees and shrubs add to the serene outdoor environment.

4.95 out of 5 average rating, 429 reviews

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 106 reviews

Cozy cottage in Harwich Port - 100 steps to beach

Newly built beachfront home in quieter Harwich Port. High-speed WiFi, open-concept living, modern kitchen with stainless appliances & quartz counters. Master with queen bed & 2nd floor deck access, 2nd bedroom sleeps 3. Central heat/AC, 3 parking spaces. Steps from beach, shops & cozy restaurants. Perfect for remote workers, weekend getaways, or anyone seeking quiet Cape Cod charm in the off-season. Experience authentic coastal living with everything you need for comfort and relaxation!

Indoor spacesKitchenGetting around

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.

4.98 out of 5 average rating, 129 reviews

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

FamilyKitchenWi-Fi

A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

4.97 out of 5 average rating, 173 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

KitchenIndoor spacesNearby

5.0 out of 5 average rating, 5 reviews

Entire Home - Steps to Beach/Downtown - Gameroom

Welcome to Dragonfly By The Sea! This beautifully renovated 4-bedroom, 2-bath + Private Outdoor Shower Cape Cod retreat features all-new 2026 furnishings, premium amenities, and a private outdoor shower. Enjoy an unbeatable location just a 1-minute walk to the beach and 5 minutes to downtown Harwich Port's shops, restaurants, cafés, and bars. Linens, towels, and professional cleaning are included. Hosted by experienced 5-star hosts dedicated to making your stay unforgettable.

FamilyIndoor spacesAmenities

Popular amenities for Harwich family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 235 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

FamilyKitchenAccuracy

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.

4.95 out of 5 average rating, 318 reviews

Slate House - a modern waterfront getaway

KitchenIndoor spacesWi-Fi

4.94 out of 5 average rating, 267 reviews

A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.

Home in South Yarmouth

Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock

Indoor spacesFamilyRiver

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

Indoor spacesKitchenAir conditioning

An outdoor entertainment area features a hot tub surrounded by a wooden deck, flanked by comfortable seating with bright cushions. A large umbrella provides shade, and a cooler displays refreshments. Colorful flowers and lush greenery enhance the tranquil ambiance of the space.

4.92 out of 5 average rating, 106 reviews

Great Chatham Location w/ Hot Tub, Near Beach!

Indoor spacesKitchenLong stay

4.94 out of 5 average rating, 114 reviews

An outdoor area showcases a gas firepit surrounded by several chairs on a stone patio, under a pergola. In the background, a deck with outdoor furniture and a hot tub is visible, complemented by a fenced yard and lush trees. Sunlight brightens this inviting space.

Home in West Yarmouth

Awesome Cottage near Beach, Backyard Bar & Hot Tub

FamilyKitchenOutdoor spaces

4.97 out of 5 average rating, 122 reviews

An outdoor patio area is visible, featuring a covered seating arrangement with comfortable couches and a dining space. An outdoor kitchen with a stone facade is present, providing an area for grilling. Sunlight filters through the pergola, enhancing the inviting atmosphere.

Home in East Falmouth

Seacoast Shores Oasis-Steps From Private Beach Bay

Indoor spacesFamilyBeach

4.9 out of 5 average rating, 330 reviews

A hot tub is situated under a wooden pergola, surrounded by trees reflecting natural greenery. Soft lighting is arranged along the structure, creating a calm ambiance. The tub is partially covered, with jets visible, inviting relaxation after a day at the beach.

Home in West Dennis

Sun Sand & Sea House- Fenced Yard and Hot Tub!

Indoor spacesKitchenDecor

Family- and pet-friendly home rentals

A spacious outdoor area features a circular arrangement of colorful chairs, including blue, red, and green options. The inviting lawn is framed by trees, with a large glassed-in porch visible in the background, providing a seamless connection to the natural surroundings.

4.93 out of 5 average rating, 116 reviews

Stunning Home in Harwich Port

KitchenIndoor spacesAir conditioning

A charming living room features a comfortable sofa with blue and white patterns, situated beside a warm gas fireplace. Sunlight filters through windows, illuminating a coffee table with a tray and snacks. Bookshelves adorned with decorative items line the walls, enhancing the cozy ambiance.

4.97 out of 5 average rating, 119 reviews

Pebbles-romantic cottage for two!

KitchenFamilyCheckout

4.93 out of 5 average rating, 162 reviews

Home in Brewster

4BR/3B | Walk2Pond | Screened Porch | FireTbl | AC

FamilyKitchenBackyard

An outdoor patio area features comfortable seating beneath a large umbrella. A grill is positioned nearby, while a spacious two-story house with light-colored shingles and numerous windows stands in the background, framed by greenery and an American flag.

4.88 out of 5 average rating, 165 reviews

Cozy and easy to beach & downtown

KitchenIndoor spacesSleep quality

4.9 out of 5 average rating, 104 reviews

A calm freshwater pond is surrounded by lush greenery and tall trees. A float is visible on the water, providing a serene spot for relaxation. Lilypads are scattered across the surface, reflecting the clear blue sky.

Guest suite in Chatham

Spacious studio on lovely pond in Chatham

FamilyKitchenSleep quality

The kitchen showcases a modern design with light cabinetry and stainless steel appliances. A round dining table with four wooden chairs is accented by a vase of sunflowers. Open shelving displays dinnerware, contributing to a bright and welcoming atmosphere.

4.96 out of 5 average rating, 56 reviews

Beautiful 1BR Steps to Wychmere Harbor & Beach

Indoor spacesFamilyLocation

4.97 out of 5 average rating, 34 reviews

Walk to Wychmere & Beach, Firepit, Fenced Yard, AC

FamilyKitchenHospitality

A modern kitchen features clean lines and a functional layout. Stainless steel appliances, including a refrigerator and microwave, are complemented by white cabinetry. A central island with a smooth countertop provides additional workspace, while bar stools offer seating for casual dining.

4.89 out of 5 average rating, 65 reviews

1 bdrm, full kitchen home, 1 mi to HarwichPort

Indoor spacesKitchenAmenities

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 100 reviews

Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

Indoor spacesKitchenAir conditioning

4.92 out of 5 average rating, 129 reviews

A communal pool area features a clear blue pool surrounded by concrete decking. Lounge chairs are arranged neatly on the sides, with greenery visible in the background. A wooden fence encloses the area, providing a private atmosphere.

Condo in Dennis Port

Sea Salt Studio - Steps to Glendon Rd Beach

Indoor spacesKitchenBarbecue

4.96 out of 5 average rating, 141 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

FamilyIndoor spacesCondition

Superhost

The exterior of the cottage features a well-maintained lawn with lush green trees in the background. A wooden deck extends from the house, along with patio chairs overlooking a tranquil pond surrounded by vibrant flowers and plants.

Cottage in Centerville

4.89 out of 5 average rating, 108 reviews

The Holly Cottage

Indoor spacesKitchenAccuracy

Guest suite in Harwich Port

A bright, airy living space features a comfortable couch, accompanied by decorative pillows. Natural light enters through a skylight and glass doors, which open to an outdoor area. A small console table holds decorative items, adding to the inviting ambiance.

4.99 out of 5 average rating, 72 reviews

The Captain's Quarters Suite - #10

FamilyIndoor spacesCleanliness

An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.

5.0 out of 5 average rating, 40 reviews

Harwich Haven: Pool & Fire Pit

KitchenIndoor spacesCleanliness

Superhost

Apartment in Dennis Port

4.86 out of 5 average rating, 14 reviews

Dennis Deluxe King Room | Full Studio w/ Kitchenet

Indoor spacesKitchenCondition

A spacious backyard is featured, highlighting a refreshing oval pool surrounded by a textured patio. Lounge chairs are positioned for relaxation under the sun. Lush greenery and trees provide a natural border, while a well-kept lawn enhances the inviting outdoor space.