Luxury Vacation Rentals in Chatham

(80 rentals)
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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 800 miles to

$286

avg/night

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Key Amenities

  • Kid friendly

About this property

Well maintained 3 bedroom home only 800 feet to Kingsbury Beach, and also a walk to Great Pond for fresh water swimming. This home features a screened porch, deck, outside shower, high speed internet and is located on a quiet sand road. Perfect location for summer family fun. Bike trail is a short bike ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 1 miles to Smugglers

$280

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

This cape house sleeps 8, 2 bathrooms, Livingroom, 3 bedrooms, kitchen with dishwasher, sunroom. stackable washer/dryer. 12 minute walk to all the Beaches; Parker's River Beach, Thatcher's and Sea View Beach. Outdoor shower, large fenced in back yard. Along route 28 is 2 mini golf, batting ...

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Property Type

Yarmouth House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.7 miles to Windmill Beach

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Unwind with a bottle of wine in this 2000 square foot home built in 2021, 3 bedrooms, 2 1/2 bath. 2 family rooms and large front porch. Open concept with kitchen island.

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Property Type

Yarmouth House

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3 BR | 2 BA | Sleeps 7 | Quick View

1

Distance to beach: 0.1 miles to Bakers Pond

$271

avg/night

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Key Amenities

  • Kid friendly

About this property

''Hilltop'' is a bright and airy newly-renovated home with easy access to beautiful Bakers Pond. Tucked up on a hill in a quiet neighborhood, this home has living areas on 3 levels, a fully-equipped kitchen and dining area (with bay windows) and opens to a large wraparound deck. Fresh ...

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Property Type

Orleans House

"Great home!"

Beautiful home with a great porch that had plenty of space for our family. The kitchen had everything and then some. Just steps away from the picturesque and clean Baker's Pond, this was a perfect place. ...

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

ONLY TWO WEEKS LEFT IN July 5 - 12th & July 12th - 19th 3 NIGHT MIN IN JUNERecently Renovated 3/1 with new kitchen & bath & close to beach w Central ACThis cozy, recently renovated cottage has a brand-new kitchen, new bathroom, and new flooring and is an excellent location, close ...

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Property Type

Brewster House

"A Restful Piece of Paradise !"

There aren't enough accolades in a dictionary to describe Shannon OR this Cape Cod cottage! Open the front door and you can't help but say "WOW!" Then walk through the three bedrooms and you'll note that ...

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Key Amenities

  • Pet friendly

About this property

Rates reflect an Early Bird special offered by owner. Rates will increase after 1/1/26. 1BR cottage with a great outdoor kitchen! Great Location across the street from the beach! Completely renovated with AC! 1BR/1BA across from the beaches on Nantucket Sound. Great outdoor kitchen and patio. Close to ...

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Property Type

Yarmouth Cottage

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Drop your bags and walk to the beach. All the comforts of home in a clean, all new and refreshed setting.Stunning West Dennis Beach a short, 4/10 of a mile walk down the picturesque Loring Ave. The home comes equipped with beach chairs, umbrella, toys, cooler, and beach wagon to make for a fun and ...

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Property Type

Dennis House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Nauset Light Beach

$257

avg/night

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Key Amenities

  • Kid friendly

About this property

This bow-roofed classic Cape features a large screened summer room with sitting and dining areas, cable TV, and floor to ceiling windows looking out on the secluded yard. The house is in a private, tree lined setting on a quiet cul de sac, one mile from Nauset Light Beach on the National Seashore. The ...

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Property Type

Eastham House

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2 BR | 2 BA | Sleeps 6 | Quick View

$257

avg/night

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Key Amenities

  • Kid friendly

About this property

Sunny 1960's style contemporary ranch in a gorgeous, private setting offers your perfect Cape Cod vacation! This one level home has 2 bedrooms and 2 updated full bathrooms with walk-in showers, a fully equipped kitchen, cozy living room and large dining room overlooking private yard. Primary Bedroom ...

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Property Type

Orleans House

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About this property

This beautifully maintained home brings on the Olde Cape Cod charm. Nestled in the heart of West Dennis, you can enjoy being less than 1/2 mile to West Dennis Beach, Kelley's Pond, and close to plenty of restaurants, shopping, and activities.This two bedroom cottage has an eat in kitchen, living ...

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Property Type

Dennis House

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Key Amenities

  • Rentals by owner

About this property

Nestled on quiet street, in a peaceful bayside neighborhood, beautifully renovated and appointed 3 Bedroom 1.5 Bath, with an enclosed outdoor shower. This pristine one-level cottage is now booking year round vacations! All new furnishings, beds and appliances!Featuring central AC, sliders to back ...

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Property Type

Eastham House

"Exceptional home away from home"

This home was so well appointed ,immaculate, and commfortable for our family.The ouside deck was the best and private. The washer and dryer and all appliances throughout the house are top notch. The laundry ...

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Studio | 4 BA | Sleeps 10 | Quick View

last minute deal
LAST MINUTE DEAL 12/23 - 1/28: Discounted Winter Rates

$250

avg/night

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Key Amenities

  • Pet friendly
  • Rentals by owner

About this property

Visit website capevaca dot com for seasonal rates and availability. From our website you can book direct, save on fees and calculate your stay. Cape Cod - Harwich on Dennis Line - Entire Home; 8 Beds - 4 Bd/2 Ba plus a seasonal outdoor shower - Linens included (a rare find on the Cape), Central ...

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Property Type

Harwich House

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DEAL

2 BR | 1 BA | Sleeps 4 | Quick View

$250

avg/night

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Key Amenities

  • Kid friendly

About this property

This bungalow cottage sits atop a bluff overlooking Cape Cod Bay in Eastham. There are two good-sized bedrooms, a full bathroom (shower), and an open concept kitchen, dining area and living room all with spectacular views of Cape Cod Bay. The house is comfortable and streamlined in its aesthetic, a lot ...

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Property Type

Eastham House

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4 BR | 2 BA | Sleeps 8 | Quick View

$243

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Oceanfront

About this property

A true Cape Cod Gem located on the edge of the National Seashore and just 2 miles to Coast Guard Beach or Nauset Light Beach! You will love coming home after a day on the beach to this private house on a wooded lot on a quiet cul-de-sac road. All the bells and whistles you want in a vacation including ...

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Property Type

Eastham House

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2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.2 miles to Bakers Pond

$243

avg/night

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Key Amenities

  • Kid friendly

About this property

Spacious two-bedroom, one level home with CENTRAL AIR-CONDITIONING sleeping six tucked up on a wooded knoll at Bakers Pond. This spot offers much privacy and is less than .1 mile to beautiful freshwater swimming and kayaking on the pond. This location feels removed from it all, yet is only a 5-minute ...

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Property Type

Orleans House

"Wonderful Location"

This house is in a wonderful location on Bakers Pond in Orleans. Easy to get to Skaket beach, Nauset Beach, 6 & all the fun spots in Orleans. Comfortable with 2 bedrooms, 2 bathrooms and big rooms with ...

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3 BR | 1.5 BA | Sleeps 6 | Quick View

Distance to beach: 0.0 miles to Cooks Brook

$243

avg/night

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Key Amenities

  • Kid friendly

About this property

Welcome to your WATERFRONT oasis in Eastham! This sunny 3-BEDROOM, 1.5-BATH home features a beautiful CATHEDRAL CEILING, providing a spacious and open feel. Enjoy BREATHTAKING VIEWS OF CAPE COD BAY from TWO SEPARATE DECKS, perfect for entertaining or relaxing with a glass of wine as you watch the sun ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly

About this property

A condo brand new in 2013 with spectacular ocean view and private ocean beach on Nantucket Sound! You wake up to the sound of the ocean wave and gorgeous view every morning! Just steps away from the private ocean beach! Master bedroom and kitchen facing ocean directly! Large sliding glass doors opening ...

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Property Type

Dennis Condo

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3 BR | 2.5 BA | Sleeps 6 | Quick View

1

Distance to beach: 2 miles to Nauset Beach

$229

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

This roomy and bright 3-bedroom, 2.5-bath home offers 2,500 square feet of living space and lots of natural light. It’s located in a quaint, private neighborhood of just 20 homes.Sleeping arrangements (all bedrooms are on 2nd floor): Primary bedroom: king bed, sitting area, and attached bathroom Second ...

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Property Type

Orleans House

"Great stay"

Our family (3 adults, 2 kids) had a wonderful week in this lovely home! The location offers plenty of privacy and space in a quiet neighborhood. The house was airy and clean, and the kitchen had pans, serving ...

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Skaket

$229

avg/night

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Key Amenities

  • Kid friendly

About this property

Location, Location! Popular duplex cottages very close to Skaket Beach on Cape Cod Bay. Informal and beachy, each unit has a private deck and central A/C! Both share the enclosed outdoor shower. No washer/dryer, but there's a clothesline for bathing suits and towels. Each unit has a full bath with ...

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Property Type

Orleans House

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Key Amenities

  • Kid friendly

About this property

Beautiful custom Cape home on the Bayside. One of the very few homes that are highly appointed yet near the beach. Nicely landscaped outside with patios and outdoor shower. Inside there is a custom dining area, bright, well equipped kitchen, living room is large, going front to back in the main house. ...

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Property Type

Eastham House

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2 BR | 1 BA | Sleeps 6 | Quick View

7

Distance to beach: 0.9 miles to Sea Gull Beach

$225

avg/night

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Key Amenities

  • Rentals by owner

About this property

Welcome aboard The Wheelhouse! Cozy 2 bedroom/1 bathroom cottage is Old Cape Cod charm at its best.Less than 3/4 mile to Sea Gull Beach, minutes from local shops, restaurants, and attractions, The Wheelhouse offers a peaceful seaside escape. You will enjoy sprawling marsh views while enjoying your ...

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Property Type

Yarmouth Cottage

"A very pleasent and quite location."

The cottage is close to every thing you need. Beaches are close by, as well as attractions and shopping. The cottage is very well equipped and comfortable in a quite location.

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4 BR | 2.5 BA | Sleeps 9 | Quick View

5

Distance to beach: 0.5 miles to Brooks Rd Beach & Earl Road Beach

$217

avg/night

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

0.3 mile walk to Brook Rd beach and 0.5 mile to Earle St beach. within 2 miles to 12 harwich Port beaches! Conveniently located in mid Cape which is the center of everything you want to go in Cape Cod! Accommodate extended familyWe provide everything you need for your vacation stay from linens ...

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Property Type

Harwich House

"Great Home and Great Location"

Regardless of the weather, we had a great week. House was very comfortable and close to everything. Can walk to a few beaches close by, but they had a lot of seaweed. If want to go to other beaches, ...

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Key Amenities

  • Rentals by owner

About this property

**All New Stainless Steel Kitchen Appliances September 2025!Private cul-de-sac 1 mile from beautiful Nauset Light Beach, 1.5 miles from Coast Guard Beach, one of the top 10 beaches in the USA year after year.Google THE BEST BEACH TOWN IN MA according to Stacker.Easy walk or bike ride to the ...

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Property Type

Eastham House

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3 BR | 2 BA | Sleeps 8 | Quick View

4

Distance to beach: 2 miles to Sea Gull Beach

$214

avg/night

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Key Amenities

  • Kid friendly
  • Pet friendly
  • Rentals by owner

About this property

Beautiful and modern family-friendly vacation getaway in West Yarmouth. This bright and inviting modern home is a great spot to use as a vacation home base. Located in the middle of it all.You’ll find our home convenient to area beaches and local attractions. Spend the day at Englewood Beach ...

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Property Type

Yarmouth House

"Perfect rental!"

My family had the best time in Denitsa's home! The house is cozy yet spacious and easily fit 7 adults. It was incredibly clean and updated, had a large yard with lots to do, and the location was perfect. ...

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Come enjoy this Cape Cod cozy home that's just a 10 minute walk from the beach. This Cape house offers tons of amenities including 2 bedrooms. One full bed other queen. Living room has a pull out queen sofa and 2 cots for extra sleeping. Outside is the best to enjoy a fire, Read in the swing ...

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Property Type

Yarmouth House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mayflower Point

$214

avg/night

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Key Amenities

  • Kid friendly

About this property

WATERFRONT COTTAGE! Nestled on two acres in Mayflower Point is this absolutely lovely, newly renovated cottage. Light and bright with cottage character throughout, painted exposed beams, skylights and glorious views out to little Pleasant Bay. Two bedrooms, one with a queen bed, the other with a bunk-bed ...

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Property Type

Orleans House

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.0 miles to Mill Pond

$214

avg/night

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Key Amenities

  • Kid friendly

About this property

Spectacular Location! An outstanding waterfront spot offering exceptional privacy. Want to unplug? This simple, rustic cottage (no wifi, no TV) is on a peninsula surrounded by salt water and has views of Mill Pond. Launch your kayak or boat from its shore to access Nauset Inlet and to the beautiful sandy ...

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Property Type

Orleans House

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to private fresh water

$207

avg/night

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Key Amenities

  • Kid friendly

About this property

Contemporary 3-bedroom, 2-bath cape-style home just 1/3 mile to Herring Pond and the scenic CC Bike Trail. With a cathedral ceiling, large deck for lounging, and an outside shower for post-adventure refreshment, this property promises a perfect blend of comfort and relaxation. Stay cool with central A/C ...

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Property Type

Eastham House

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3 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 900 miles to Kingsbury

$200

avg/night

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Key Amenities

  • Kid friendly

About this property

Fresh and Salt Water Beaches! This 3-bedroom home (960 sq/ft) is located at the end of a quiet sand road within a short walk (700ft) to Kingsbury Beach. Features include a wraparound deck, and glassed-in sun porch. Wiley Park (Great Pond) is a mere 1/3 mile walk for fresh water swimming. Amenities include ...

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Property Type

Eastham House

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Key Amenities

  • Kid friendly
  • Rentals by owner

About this property

Smell the fresh New England air of Cape Cod. Two bedrooms, 1 with queen size bed, second bedroom with bunk beds. Open Concept living room and kitchen with TV and brand new floors! Shower inside or outside- offering an updated inside bathroom with shower as well as outside shower. Outside patio with table, ...

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Property Type

Dennis Cottage

"Perfect location"

Adorable little cottage! The host was a really great person. The location was a close walk to the beach. There was a lot to do and pretty close to everything.

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Chatham Vacation Rentals