South Chatham, MA Vacation Homes from AED 1,124

South Chatham Vacation Homes
Massachusetts
United States of America
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Our top choices for South Chatham vacation homes

A beach with a rocky shoreline, clear blue sky, and houses in the background.

A modern kitchen with wooden cabinets, a large island with bar stools, and a skylight.

A spacious living room with a large brown leather sofa, a round wooden coffee table, and a view of the backyard through large windows.

A kitchen with wooden cabinets, a microwave, stove, sink, and a skylight.

1. Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8

Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8

Chatham

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Great house in a wonderful location! Would definitely stay again!"

Kelly M.

Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8

A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

A laundry room with two washing machines, a shower curtain, and a towel rack.

A single-story house with a grey roof, white trim, and a pink door.

A bedroom with a bed, a ceiling fan, a window, and a dresser.

2. Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham

9.8 out of 10, Exceptional, (106 reviews)

9.8/10

Exceptional

(106 reviews)

"Excellent location and stay at the lucky 7 cottage. The communication with the host was outstanding, best I’ve experienced. We’ll definitely be back for another time at this location."

Mark K.

The price is AED 422

AED 422

AED 1,982 total

includes taxes & fees

3 Nov - 4 Nov

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

A sandy beach with a grassy path leading to the water.

A two-story house with a front porch, a mailbox, and a number 248 on the door.

A modern kitchen with a stainless steel refrigerator, white cabinets, a built-in sink, and a wooden floor.

A modern kitchen with white cabinets, stainless steel appliances, and a window providing natural light.

3. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail

Chatham

9.8 out of 10, Exceptional, (90 reviews)

9.8/10

Exceptional

(90 reviews)

"Beautiful, clean home with very responsive and kind hosts!"

Claire D.

The price is AED 992

AED 992

AED 2,257 total

includes taxes & fees

4 Oct - 5 Oct

Beautiful home near Jacknife Beach and bike trail

A two-story house with a front porch, a chimney, and a well-maintained lawn.

A modern kitchen with white cabinets, stainless steel appliances, a marble countertop, and a small island with two bar stools.

A wooden deck with a picnic table and wicker chairs, surrounded by a white picket fence and greenery.

A gravel path leading to a small shed surrounded by lush greenery and flowering plants.

4. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!

Harwichport

9.8 out of 10, Exceptional, (82 reviews)

9.8/10

Exceptional

(82 reviews)

"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"

John N.

The price is AED 1,157

AED 1,157

AED 3,002 total

includes taxes & fees

4 Oct - 5 Oct

Family Cottage Close to Beach!!

A resort with a large pool, sun loungers, and a pier extending into the water.

A large, two-story house with a balcony overlooking a body of water, surrounded by lush greenery.

A covered outdoor dining area with multiple tables and chairs, overlooking a body of water.

A living room with a sofa, coffee table, and a television. There is a staircase leading to another room.

5. Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort

Harwich

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"Great host. Convenient location for a visit to Chatham."

Bill F.

The price is AED 463

AED 463

AED 1,761 total

includes taxes & fees

5 Oct - 6 Oct

Cozy Large Home in Harwich with Patio near Wequassett Resort

An outdoor patio with Adirondack chairs, a fire pit, and string lights.

A modern kitchen with a marble island, four bar stools, a stainless steel refrigerator, and a clock on the wall.

A residential driveway leading to a house with a stone wall and steps.

A modern living room with a grey sofa, a fireplace, and a kitchen in the background.

6. Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Harwich

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Excellent location "

Norman Y.

The price is AED 863

AED 863

AED 2,569 total

includes taxes & fees

4 Oct - 5 Oct

Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

A lighthouse with a cylindrical tower and a white building with a red roof.

A wooden desk with a laptop, a fan, and a "Relax" sign on the wall.

A beach with boats moored in the water and a sandy shore.

A living room with a white cabinet, striped armchair, and a wicker chair.

7. Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham

10.0 out of 10, Exceptional, (128 reviews)

10/10

Exceptional

(128 reviews)

"Amazing stay so close to town and CBI."

Joanne B.

The price is AED 826

AED 826

AED 2,035 total

includes taxes & fees

3 Nov - 4 Nov

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

A residential property with a well-maintained lawn, a white picket fence, and flowering plants.

A two-story wooden house with a front porch, a small attached garage, and a fenced yard.

A golf course with a pond, surrounded by dense trees and a clear sky.

8. Seaside Getaway - Harwichport Beachhouse

Seaside Getaway - Harwichport Beachhouse

Harwich

9.2 out of 10, Wonderful, (17 reviews)

9.2/10

Wonderful

(17 reviews)

"Great stay! Clean and comfortable and close to town."

Meredith R.

The price is AED 889

AED 889

AED 1,871 total

includes taxes & fees

5 Oct - 6 Oct

Seaside Getaway - Harwichport Beachhouse

A bedroom with a bed, a desk, a chair, a TV, and a window.

A compact kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

A backyard with a wooden deck, outdoor furniture, and a barbecue grill.

A modern living room with a sofa, dining table, and chairs, a fireplace, and a TV mounted on the wall.

9. Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

Harwich

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

The price is AED 1,322

AED 1,322

AED 1,934 total

includes taxes & fees

4 Oct - 5 Oct

Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

A spacious living room with a large sliding glass door leading to an outdoor patio, a ceiling fan, and a white sofa with patterned cushions.

A spacious living room with a high ceiling, a white sofa with blue cushions, a brown leather armchair, a wooden coffee table, and a small side table with books.

A modern kitchen with white cabinets, a granite island, stainless steel appliances, and pendant lighting.

A kitchen with a modern faucet, a window with a view of greenery, and a countertop with fruits.

10. Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

West Brewster

10.0 out of 10, Exceptional, (37 reviews)

10/10

Exceptional

(37 reviews)

"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"

Jim M.

The price is AED 637

AED 637

AED 2,730 total

includes taxes & fees

5 Oct - 6 Oct

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

A wooden interior with a sofa, coffee table, TV, and kitchen area.

A kitchen with wooden cabinets, a stove, a sink, and a dining area with a table and chairs.

A wooden cabin interior with a kitchen, dining area, and a door with a window.

11. Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Dennis Port

4.0 out of 10, (1 review)

4.0/10

(1 review)

"Excellent vacation in a great spot but the property needs some care."

Art E.

The price is AED 312

AED 312

AED 1,689 total

includes taxes & fees

4 Oct - 5 Oct

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

A modern outdoor pool area with a hot tub, lounge chairs, and a deck overlooking a residential property.

A spacious living room with a high ceiling, a fireplace, a large flat-screen TV, and a comfortable seating area with sofas and cushions.

A spacious living room with a large sectional sofa, a coffee table, and a view of a swimming pool.

An outdoor patio with a wooden table and wicker chairs, a pool area with lounge chairs, and a view of the surrounding greenery.

12. Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen

Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen

Chatham

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"We had an awesome week! The entire family loved your beautiful house and couldn’t stop talking about that view! One of our BEST family vacations. Thanks for making it so special!!"

julie g.

Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen

A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

A rustic wooden shed, a picnic table, and a striped umbrella in a wooded backyard.

A kitchen with wooden cabinets, a microwave, a toaster, and a sink.

A small white building with blue shutters, a door, and a number '26' on the side.

13. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Dennis Port

9.2 out of 10, Wonderful, (27 reviews)

9.2/10

Wonderful

(27 reviews)

"Property is convenient to beaches and restaurants."

Laurie and Rick A.

The price is AED 250

AED 250

AED 1,590 total

includes taxes & fees

5 Oct - 6 Oct

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

A beach with footprints, a large rock, and a clear sky.

A backyard with a fire pit, outdoor seating, and a house.

A coastal hotel with a paved walkway leading to a seating area, surrounded by lush greenery and a view of the sea.

A living room with a grey sofa, a wooden coffee table, and a vase of flowers.

14. The Brewster Pearl

The Brewster Pearl

Brewster

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"The home is so beautiful and the decor is like out of a magazine. Immaculately clean, our standards are high, being hosts ourselves. Every amenity thoughtfully provided. The furnishings, bedding, towels are of premium quality and top brand. Our host was incredible, responsive, kind and helpful. This home is perfectly located to many beaches , excellent restaurants and coffee shops. Brewster is a special place. I can understand why the owner chose it. Our family was immensely blessed to have the...

PAULA

The price is AED 790

AED 790

AED 2,451 total

includes taxes & fees

3 Nov - 4 Nov

The Brewster Pearl

A house with a wooden deck, a brick chimney, and a porch with wicker furniture.

A small shed with an open door, revealing storage shelves and a wooden ramp leading to the entrance.

A room with a wooden ceiling, a window with blinds, a star decoration, and a table with items.

A dining room with a long table set for a meal, white walls, and large windows.

15. Charming Dennis Port Retreat Near the Beach

Charming Dennis Port Retreat Near the Beach

Dennis Port

7.4 out of 10, Good, (6 reviews)

7.4/10

Good

(6 reviews)

The price is AED 661

AED 661

AED 1,927 total

includes taxes & fees

4 Oct - 5 Oct

Charming Dennis Port Retreat Near the Beach

A cozy living room with a sectional sofa, a fireplace, and wooden walls.

Dennis Port Vacation Rental | 2BR | 1BA | 1,000 Sq Ft | 2 Steps Required

A wooden interior with a dining table, chairs, a clock, and a stove.

A small house with a front porch, a white door, and a mailbox. There are two chairs in the yard.

16. Family-Friendly Home! Walk to Sea Street Beach

Family-Friendly Home! Walk to Sea Street Beach

Dennis Port

6.4 out of 10, (5 reviews)

6.4/10

(5 reviews)

"Location was great! Cozy house. Easy to get in touch with host. Bathroom could use update. "

Devin L.

Family-Friendly Home! Walk to Sea Street Beach

A spacious living area with a sofa, chairs, a fireplace, and a kitchen in the background.

A dining area with a round table, chairs, and a ceiling fan.

A bedroom with a bed, a ceiling fan, a window with curtains, a bedside table with a lamp, and a framed picture on the wall.

A modern kitchen with white cabinetry, a large island, stainless steel appliances, and a skylight.

17. Lovely 3-bedroom house in Dennis perfect for a relaxing getaway

Lovely 3-bedroom house in Dennis perfect for a relaxing getaway

Dennis

The price is AED 992

AED 992

AED 2,615 total

includes taxes & fees

4 Oct - 5 Oct

Lovely 3-bedroom house in Dennis perfect for a relaxing getaway

An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

A living room with a fireplace, sofas, a coffee table, and a television.

A residential house with a front yard, a driveway, and a wooden fence.

A living room with two sofas, a coffee table, and a chair. There is a door with a blue frame and a window with curtains.

18. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis

10.0 out of 10, Exceptional, (205 reviews)

10/10

Exceptional

(205 reviews)

"Great location and great host!! We’ll be back!!!"

Patrick T.

The price is AED 314

AED 314

AED 1,124 total

includes taxes & fees

14 Oct - 15 Oct

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

A modern kitchen with white cabinets, a wooden ceiling, and a herringbone-patterned floor.

A two-story house with a large front porch, multiple windows, and a well-maintained lawn.

A beach with sand and tall grass in the foreground, a clear sky, and a calm sea.

A kitchen counter with a cutting board holding various cheeses, cured meats, and two glasses of white wine.

19. Beach Bungalow: Steps to Beach, Luxury Family Fun

Beach Bungalow: Steps to Beach, Luxury Family Fun

Harwich

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"We had an excellent stay on the cape at this beautiful home that was walking distance to the beach. The location was perfect and neighborhood was exactly what we dreamed of for an offseason getaway."

Christopher R.

The price is AED 1,018

AED 1,018

AED 2,569 total

includes taxes & fees

3 Nov - 4 Nov

Beach Bungalow: Steps to Beach, Luxury Family Fun

A modern two-story building with large windows and a flat roof.

A modern kitchen with white cabinets, a built-in oven, and a dining area with a table set for four.

A modern living room with a sofa, coffee table, and dining area.

A living room with a blue sofa set, a coffee table, a TV stand, and a fireplace.

20. Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

Dennis Port

9.8 out of 10, Exceptional, (17 reviews)

9.8/10

Exceptional

(17 reviews)

"The property was great and hope to be back in the future."

Jason H.

Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top South Chatham Hotel Reviews

Sunbird Cape Cod Resort

8/10 Good

"will come back."

Robert 2-night trip

Posted 2 hours ago

Sunbird Cape Cod Resort

Lighthouse Inn

10/10 Excellent

"Loved the cottage! Beautiful view! Staff was lovely!"

Joanne 1-night trip

Posted 14 hours ago

Lighthouse Inn

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent

"Everything was perfect"

Paul 2-night trip

Posted 15 hours ago

Uncommoner Hotel by Reverie Boutique Collection

Riviera Beach Resort

10/10 Excellent

"Perfect location, right on the beach and easy access to all the surrounding towns."

CATHY 2-night trip

Posted 16 hours ago

Riviera Beach Resort

Chatham Tides

10/10 Excellent

"We loved this quaint quiet hotel off the main drag and with its private beach! bikes and grills provided were a bonus. Staff were beyond helpful! Will definitely return!!!"

christina 4-night trip

Posted 3 days ago

Chatham Tides

Hyannis Travel Inn

10/10 Excellent

"Clean rooms and very helpful staff."

Louie 1-night trip

Posted 3 days ago

Hyannis Travel Inn

Hyannis Plaza Hotel

10/10 Excellent

"Todo está muy bien y en buena ubicación"

jimmy 1-night trip

Posted 6 days ago

Hyannis Plaza Hotel

The Corsair & Cross Rip Oceanfront Resort

10/10 Excellent

"Great location and amenities. 3 pools and private beach. Would definitely stay there again!"

Timothy Jon 3-night trip

Posted 6 days ago

The Corsair & Cross Rip Oceanfront Resort

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

10/10 Excellent

"Very friendly staff. Great breakfast ."

Joyce 3-night trip

Posted 7 days ago

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Search Vacation Homes in South Chatham

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Chatham vacation homes

1. Relaxing Cape Escape • Family Retreat • Walk to Beach • 6 beds • Sleeps 8

2. Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

3. Beautiful home near Jacknife Beach and bike trail

4. Family Cottage Close to Beach!!

5. Cozy Large Home in Harwich with Patio near Wequassett Resort

6. Wychmere Weddings, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

7. Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

8. Seaside Getaway - Harwichport Beachhouse

9. Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

10. Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

11. Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

12. Luxury Coastal Retreat Overlooking Buck's Creek and Nantucket Sound — Pool, Hot Tub, Outdoor Kitchen

13. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

14. The Brewster Pearl

15. Charming Dennis Port Retreat Near the Beach

16. Family-Friendly Home! Walk to Sea Street Beach

17. Lovely 3-bedroom house in Dennis perfect for a relaxing getaway

18. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

19. Beach Bungalow: Steps to Beach, Luxury Family Fun

20. Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

Find vacation rentals that suit your style

Top South Chatham Hotel Reviews

Sunbird Cape Cod Resort