Holiday houses in Oyster Pond

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Top-rated holiday rentals in Oyster Pond

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

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Guest favourite

A serene coastal scene captures the sandy beach leading to calm waters under a clear blue sky. Sparse vegetation and gentle waves frame the horizon, where distant land meets the sea. The tranquil setting invites peaceful reflections and scenic walks along the shore.

Apartment in Chatham

Chatham with Private Beach

Just park your car and enjoy this beautiful location. Private beach with walking paths to lighthouse beach and Monomoy. This Condo has views of the beautiful Chatham sandbars from the front Adirondack chairs, deck with grill and dining table or steps to a private beach. Inside the Condo has a fully appointed kitchen. Sofa and Love seat, wall mounted TV and dining table. Updated bathroom with full tub. First floor bedroom with queen bed and loft with queen bed, dedicated work space and twin bed

5.0 out of 5 average rating, 12 reviews

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

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

4.97 out of 5 average rating, 295 reviews

Top Guest favourite

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.

4.99 out of 5 average rating, 670 reviews

Guest favourite

A charming two-story home is situated amidst well-maintained landscaping, featuring a mix of green shrubs and colorful foliage. The exterior is characterized by a traditional wood shingle design, and multiple windows allow natural light to enter the interior spaces.

Home in Chatham

Walk to Beach and Town, newly renovated 4/BR

Enjoy easy access to everything from this perfectly located home base. Located in historic Chatham Village, this 1850's home is a minute walk from Oyster Pond beach, down town, and the ball park. House has been completely updated and refreshed with new first floor bathroom, and new granite in kitchen. House has 4 bed rooms, three with queen sized beds, and one with twin bunks. Master bedroom has adjacent sitting room with fold out day bed providing privacy and additional sleeping area.

4.96 out of 5 average rating, 48 reviews

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

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!

4.97 out of 5 average rating, 120 reviews

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

Renovated Chatham Windmill! Walk to Beach/Town!

**Airbnb service fees are now included in nightly rate.** ----------Renovated Chatham Windmill! Beautiful Water View, Steps to Oyster Pond Beach & Main Street! 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!

4.96 out of 5 average rating, 89 reviews

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

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.

4.97 out of 5 average rating, 178 reviews

Top Guest favourite

An open concept living area features a comfortable white couch and armchair, with a wooden coffee table at the center. The kitchen, visible in the background, is well-equipped and includes a fridge, while a dining area with two stools is highlighted. Natural light brightens the space.

Holiday home in Chatham

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

5.0 out of 5 average rating, 78 reviews

Superhost

Home in Chatham

NEW! Coastal Luxury - Spacious, Game Room, Firepit

Welcome to Chatham Vacation, a newly renovated Cape Cod retreat perfect for families, two families traveling together & multi-generational getaways. Enjoy professionally designed coastal interiors, a chef’s kitchen, spacious deck, fire pit, game room, workspace & peaceful pond views. - Walking distance to Stillwater Pond - 4 min to Jackknife Beach - 6 min to Wequassett Resort & Golf Club - 7 min to Downtown Chatham Experience Chatham with us & learn more below!

5.0 out of 5 average rating, 4 reviews

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

Storm watch. Warm inside, walk to ocean.

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**

4.97 out of 5 average rating, 409 reviews

Top Guest favourite

A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.

Home in Chatham

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

5.0 out of 5 average rating, 29 reviews

Top Guest favourite

A serene view of a calm harbor filled with various boats, all anchored in the water. The foreground features a grassy area with a wooden path leading toward the water's edge, while vibrant greenery and flowers are visible along the border.

Home in Chatham

Oceanfront Chatham Village Home

Quiet Peaceful Oceanfront Home, Short Walk to Chatham Village and Walk to Lighthouse Beach. Sleeps 12. Large kitchen, stainless steel appliances, gas stove. Every Room except one room has amazing ocean views! Stone patio overlooks Ocean Harbor on Little Mill Pond. A Video Walkthrough of the house, featured by Eileen Cotter of Pure Wander: https://www.youtube.com/watch?v=_tqi6m8-1zs&t

4.97 out of 5 average rating, 103 reviews