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Holiday houses in Chatham

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Top-rated holiday rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The main living area features white slipcovered sofas surrounding a central coffee table, with a cozy electric fireplace situated beneath a wall-mounted smart TV. Large windows provide ample natural light and a view of the outdoor space, enhancing the room's bright ambiance.
Home in Chatham
5 out of 5 average rating, 52 reviews

Downtown Chatham Home w/ Patio - Near Oyster Pond

This stunning historical home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, Oyster Pond, movie theater, Veterans Field for Chatham A’s games & more! This cozy home is perfect for a family, group of friends, or couples with two living areas, an outdoor patio with lounge areas, a large dining table, grill & fire pit. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

FamilyLocationLayout

Top Guest favourite
A spacious roof deck features a dining table with seating for eight, shaded by a vibrant red umbrella. A lounge area showcases comfortable seating against a backdrop of a beautiful sunset. A grill and a cornhole game add to the outdoor enjoyment.
Home in Chatham
5 out of 5 average rating, 13 reviews

Luxury Home- Chatham Center- Walk to Town + Beach

Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is perfect for families, couples, or a group of friends looking to be walking distance to restaurants, boutiques, the beach & so much more! Enjoy an extremely spacious home with almost 2,700 sq ft of living space, 3 ensuites, & a large roof deck. In Downtown Chatham .3 Miles to Oyster Pond .5 Miles to Seaside Links Golf Course Experience Chatham with us & learn more below!

LocationSleep qualityHospitality

Guest favourite
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
4.96 out of 5 average rating, 312 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

LocationValueLaundry

Top Guest favourite
A charming cottage with a shingle exterior is framed by a vibrant yard. A white picket fence encloses flower beds, and a small patio features an umbrella for shade. A welcoming pathway leads to the front door, surrounded by greenery and a manicured lawn.
Cottage in Chatham
4.97 out of 5 average rating, 295 reviews

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property

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Top Guest favourite
A sun-filled living room features large windows allowing natural light to illuminate the space. Two rocking chairs are positioned beside a comfortable sofa. A wooden coffee table sits at the center, with a media console and wall-mounted TV offering entertainment options.
Home in Chatham
4.97 out of 5 average rating, 31 reviews

Close to Beach Renovated Dog Friendly Cape Cottage

Welcome to our enchanting Cape Cottage in the heart of Chatham, where timeless charm meets modern comfort. 4 minutes from the beach and nestled on a spacious half acre, this newly revitalized and renovated home provides an authentic Cape Cod vacation experience. As you step into our home, you'll immediately sense the true heart and soul of a Cape Cod getaway. Our cottage boasts a warm and inviting atmosphere, perfect for families, couples, or friends seeking a luxurious escape to Chatham.

ValueLocationQuiet

Top Guest favourite
The exterior of a spacious house is shown, featuring a large front porch with a gentle slope and decorative flowers. An attached garage is visible, and the well-manicured lawn surrounds the property. A private gravel driveway leads to the entrance, shaded by trees under a clear blue sky.
Guest suite in Chatham
4.99 out of 5 average rating, 132 reviews

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

ValueFamilyCleanliness

Top Guest favourite
A charming beach house with shingle-style siding is displayed, set within a landscaped yard. Two large bushes frame the entryway, and the building features multiple rooflines and skylights. A brick pathway leads to the front door, with trees providing partial shade in the foreground.
Home in Chatham
4.97 out of 5 average rating, 115 reviews

Beachfront Charmer! Newly Renovated.

Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

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Top Guest favourite
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.
Home in Chatham
4.97 out of 5 average rating, 172 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.

ValueFamilyAir conditioning

Superhost
A charming cottage exterior is showcased, featuring natural wood siding and flower boxes below the windows. The entrance is framed by shrubs, while a grassy area surrounds the cottage. Mature trees provide shade, enhancing the peaceful setting in a tree-filled neighborhood.
Home in Chatham
4.84 out of 5 average rating, 159 reviews

Delightful Chatham Cottage, Cheerful and Clean

AirBnB Superhost, local owner has 25 years of online vacation rental experience with this property. Refreshed and updated , our 1 bedroom cottage is an ideal getaway spot for a couple or young family. The cottage is located on a 1/2 acre lot in the geographical center of Chatham, on a private road in a quiet, tree-filled neighborhood. Guests all agree that we have a fantastic location at an affordable price. Enjoy a relaxing stay while being close to everything in town.

FamilyValueAmenities

Top Guest favourite
The inviting living area features large windows with blue curtains, allowing natural light to brighten the space. A comfortable sectional sofa is situated around a small coffee table. A door leads to a private balcony, while a bar counter with stools is visible in the background.
Condo in Chatham
4.97 out of 5 average rating, 384 reviews

Private Pied-a-Terre, in-village hidden Oasis.

Great in-town location. Bright, Clean, Safe, Private and Spacious. Hidden away Above the shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Well equipped Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

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Top Guest favourite
The renovated windmill exterior showcases unique architectural features with a pointed roof and prominent wooden blades. A bright blue door is framed by a brick pathway, leading to a garden of blooming daffodils, offering a cheerful first impression.
Cottage in Chatham
4.95 out of 5 average rating, 80 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

Newly renovated Chatham Windmill! Beautiful Water View, Steps to Oyster Pond Beach & Main Street! Complete renovation of Windmill in 2022. This unique rental has one bedroom with king bed on second floor, with small full kitchen/dining area, two sitting/TV areas and full bathroom on first floor. Private patio with BBQ grill, dining table and chairs. Enjoy the beautiful water view from Adirondack chairs, just outside your door! Perfect spot for your vacation!

ValueFamilyLayout

Top Guest favourite
A spacious living room features a comfortable blue sectional sofa and a white armchair, arranged around a wooden coffee table. A modern floor lamp provides soft lighting. A fireplace is flanked by built-in shelves displaying books and decor, with large windows allowing natural light to fill the space.
Home in Chatham
5 out of 5 average rating, 13 reviews

Walkable to Downtown Chatham Home with Bikes

Escape to The Nook on Nob Hill, a stylish 3BR/1BA Cape Cod getaway in Chatham for 6. Just a 5-min walk to downtown and steps from the Cape Cod Rail Trail. Enjoy modern coastal charm, a fully equipped kitchen, a fire pit, and family-friendly amenities. Perfect for families and outdoor lovers seeking a convenient and comfortable base to explore the Cape. Recently named a top Fall stay by Capeology!

LocationFamilyBiking

Popular amenities for Chatham holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Chatham

Guest favourite
Cottage in Chatham
4.95 out of 5 average rating, 65 reviews

Chit-Chat Cottage on White pond, near DT/beaches.

LocationFamilySleep quality

Superhost
The living area features a sectional sofa and two armchairs in light blue, arranged around a coffee table. A 55” smart TV is positioned on a media console, while windows allow natural light to fill the space. Air conditioning units are mounted for comfort.
Condo in Chatham
4.79 out of 5 average rating, 100 reviews

Lavish Downtown Chatham Condo: Walk to Everything!

ValueFamilyHiking

Home in Chatham
5 out of 5 average rating, 3 reviews

Relaxing Cape Escape • Walk to Beach • 6 Beds

LocationFamilyGetting around

Top Guest favourite
Home in Chatham
5 out of 5 average rating, 16 reviews

Meadow + Main

LocationValueHospitality

Top Guest favourite
Home in Harwich
4.98 out of 5 average rating, 42 reviews

The Hideaway - Harwich Port Getaway

FamilyValueNearby

Guest favourite
A functional kitchen features light-colored tile flooring and wooden cabinetry. A double sink is positioned beneath a window, and a stove is located adjacent to a refrigerator. Counter space is available on both sides, with additional storage cabinets visible.
Home in Chatham
4.93 out of 5 average rating, 54 reviews

Chatham Beach Cottage

LocationValueSleep quality

Guest favourite
The exterior of a charming beach cottage features weathered cedar shake siding and well-maintained landscaping. A welcoming pathway leads to the entry door, flanked by two sets of windows adorned with flower boxes. The lawn is landscaped with shrubs and mulch.
Home in Chatham
4.97 out of 5 average rating, 33 reviews

Charming Chatham Cottage

FamilyLocationOutdoor spaces

Guest favourite
A cozy sleeping area features a spacious bed with a light coverlet and two accent pillows. Artwork in various frames adorns the wall above, complemented by wall-mounted sconces. A small bedside table holds books and a decorative plant, enhancing the room's inviting ambiance.
Home in Chatham
5 out of 5 average rating, 8 reviews

New! Chatham Cozy Cottage on White Pond

LocationWalkabilityComfort

When is the best time to visit Chatham?

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Avg. price$421 AUD$435 AUD$442 AUD$445 AUD$514 AUD$606 AUD$785 AUD$785 AUD$532 AUD$481 AUD$502 AUD$492 AUD
Avg. temp0°C0°C3°C7°C12°C17°C21°C21°C18°C13°C8°C3°C

Frequently Asked Questions

  • What are the best places to stay in Chatham?

    Chatham has a range of stays near beaches, the historic village area, and Main Street. Many visitors seek accommodations with scenic views or easy access to local shops and trails.

  • What are the best things to do in Chatham with kids?

    Families often explore sandy beaches, interactive museums, and nature trails. Chatham also has casual dining options and ice cream shops that welcome kids.

  • What are some of the best things to do in Chatham?

    Explore sandy beaches, visit the iconic lighthouse, and stroll the shops and galleries along Main Street. Nature reserves and boat tours show coastal habitats, offering a variety of outdoor experiences.

  • How is the weather in Chatham?

    Chatham has chilly, wetter winters near 25–44°F (-4–7°C), while summers are mild and bring temperatures between 63–76°F (17–24°C). Layers and a waterproof jacket are useful year-round.

  • When is the best time to visit Chatham?

    Late spring through early autumn is often recommended for milder temperatures between 48–76°F (9–24°C) and generally fewer rainy days. Summer draws visitors for beaches and seasonal festivities.

  • What are the best places to visit in Chatham?

    Chatham Lighthouse, Main Street's shops and galleries, and sandy beaches are frequently suggested. Local museums and conservation areas invite exploration of maritime history and nature.

  • What are some hiking trails in Chatham?

    Chatham has nature trails winding through salt marshes, woodlands, and conservation lands. Community parks and protected areas are often suggested for gentle hikes and birdwatching.

  • What are some family activities we can do in Chatham?

    Visit sandy beaches, play in community parks, tour maritime museums, and spot seals near the lighthouse. Seasonal events and outdoor picnics on trails are often enjoyed by families.

  • What are some of the best day trip ideas from Chatham?

    Explore nearby Cape Cod towns, local nature reserves, or take a ferry to see coastal islands. Art galleries, historic sites, and outdoor adventures are frequently suggested for day trips around the area.

  • Are there any pet friendly accommodations available in Chatham?

    Many accommodations in Chatham welcome pets, especially around Main Street, the village area, and beach neighborhoods. Parks and walking trails make it easy to get outside with your dog.

  • What are some local tips for visiting Chatham?

    Locals often suggest booking popular restaurants and activities in advance during summer. Early morning beach walks and exploring markets around Main Street are favorites for a quieter experience.

  • What is Chatham known for?

    Chatham has sandy beaches, a scenic lighthouse, and a lively pedestrian-friendly Main Street. It is often recognized for its maritime history, local seafood, and coastal charm.

  • What are the best hidden gems to explore in Chatham?

    Walk through serene conservation areas, discover tucked-away art galleries, or find quiet coves for beachcombing. Small markets and lesser-known nature trails around Chatham reward curious explorers.

  • What are the best foods to try in Chatham?

    Locally caught seafood is frequently suggested, including clam chowder, lobster rolls, and oysters. Bakeries and ice cream shops around Main Street feature seasonal treats and classic desserts.

  • What should I bring for a trip to Chatham?

    Pack layers, a light waterproof jacket, and comfortable walking shoes for strolling beaches or exploring town. Sunscreen, hats, and reusable water bottles are handy for outdoor activities.

  • What is the nightlife in Chatham like?

    Chatham has casual nightlife centered around pubs, restaurants, and occasional live music spots. Evening gatherings often highlight seasonal outdoor concerts and relaxed dining.

  • What are the most popular events or festivals in Chatham?

    Chatham has summer art fairs, Fourth of July parades, and holiday strolls in winter. Local concerts and community celebrations are often recommended, especially during peak visitor seasons.

  • Are there family friendly vacation rentals in Chatham?

    Chatham has a range of family friendly vacation rentals, including cottages, larger homes, and condos near beaches and downtown. Many stays feature amenities like backyards and proximity to parks.

Quick stats about holiday rentals in Chatham

  • Total holiday rentals

    Explore 540 holiday rentals in Chatham

  • Nightly prices starting at

    Chatham holiday rentals start at $86 AUD per night before taxes and fees

  • Verified guest reviews

    Over 19,870 verified reviews to help you choose

  • Family-friendly holiday rentals

    480 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 210 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wi-Fi availability

    540 of Chatham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Beachfront, Gym and BBQ grill across Chatham rentals

  • 4.9 Average rating

    Chatham stays are highly rated by guests—averaging 4.9 out of 5!

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