South Chatham Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for South Chatham hotels

A room with a bed, two wicker chairs, a small table, a coffee maker, and a view of the sea through a window.

A beachfront property with a wooden deck, a sign labeled "SHOWER," and surfboards stored outside.

A modern kitchen with white cabinets, a built-in oven, and a view of the ocean through large windows.

A room with a large window overlooking the sea, a white desk, and nautical-themed decor.

1. Chatham Tides

South Chatham

Craig

฿5,402

฿6,182 total

includes taxes & fees

10 Nov - 11 Nov

A house with a brick exterior, white exterior walls, and a front porch with white chairs.

A bedroom with a bed, a nightstand, a lamp, a window with curtains, a hat, and a magazine on the bed.

A beach with a fallen tree, clear blue water, and a forested shoreline.

A white desk with a woven hat, a vase with white flowers, and two glasses of white wine.

2. Chatham Seafarer Inn

Chatham

Ian

฿7,808

฿8,936 total

includes taxes & fees

14 Oct - 15 Oct

A sign for Handkerchief Shoals Inn with a well-maintained garden in the foreground.

A bedroom with a bed, a table, two chairs, a lamp, and a window with curtains.

A reception area with a counter, a blue door labeled "Office," and a wall-mounted shelf with various items.

An outdoor patio with round tables and chairs, picnic tables, and umbrellas.

3. Handkerchief Shoals Inn

South Harwich

Matthew

฿5,975

฿6,838 total

includes taxes & fees

13 Oct - 14 Oct

A swimming pool with blue water, surrounded by lounge chairs and a waterfall feature.

A bedroom with a large bed, two side tables with lamps, a wooden nightstand, a wooden dresser, and a large window with a view of greenery.

A circular wooden structure with illuminated edges in a garden setting.

A house surrounded by dense trees and a gravel path leading to the front door.

4. Pleasant Bay Village Resort

Chatham

sheila

฿8,098

฿9,268 total

includes taxes & fees

13 Oct - 14 Oct

A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.

A garden with a pergola structure, a pathway, and a seating area.

An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.

A restaurant with long communal tables and booths, large windows, and a view of buildings outside.

5. Chatham Wayside Inn

Chatham

Ashley

฿6,005

฿8,332 total

includes taxes & fees

1 Nov - 2 Nov

Four sun loungers aligned along a poolside with a tiled floor.

A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.

A covered porch with white columns and a pathway leading to a door.

A modern bedroom with a wooden wardrobe, a white robe hanging on the door, and a bed with a wooden frame.

6. Greyfinch Chatham Inn

Chatham

Jacob

฿5,703

฿7,756 total

includes taxes & fees

1 Nov - 2 Nov

A two-story residential building with a well-maintained lawn, a wooden fence, and a patio area with outdoor furniture.

A modern bathroom with a glass shower enclosure, a white sink, and a towel rack.

A cozy living room with a fireplace, striped sofa, wooden flooring, and exposed beams.

A beach with clear water, a sandy shore, and houses in the background.

7. Kingfisher Harwich Port

Harwich Port

Marc

฿6,070

฿6,947 total

includes taxes & fees

13 Oct - 14 Oct

A two-story house with a well-lit front porch, a staircase leading to the entrance, and a garden with various plants and flowers.

A large swimming pool with a fountain, surrounded by lounge chairs and umbrellas, set against a stone building with multiple windows and a balcony.

A corner building with a curved roof, large windows, and a well-maintained garden with various plants and flowers.

A large, two-story house with a covered patio area, outdoor seating, and a stone waterfall feature.

8. Winstead Inn

Harwich

Karen

฿7,544

฿8,635 total

includes taxes & fees

19 Oct - 20 Oct

A two-story house with a front porch, a mailbox, and a well-maintained garden.

A modern interior with a wooden floor, a blue and white patterned wall, a large painting, and a bar area with a blue marble backsplash.

A hotel room with a bed, a bench, a desk, a microwave, and a television.

A swimming pool with lounge chairs and a covered seating area.

9. Pelham on Earle

West Harwich

Colleen

฿6,337

฿7,833 total

includes taxes & fees

26 Oct - 27 Oct

A coastal scene with a large group of seals resting on the shore.

A set of outdoor brick steps leading to a building with a white balcony.

A house with a grassy yard and a view of the water.

A coastal view with a beach, boats, and a house with a lawn and lamp post.

10. The Hawthorne

Chatham

Richard

฿11,028

฿12,621 total

includes taxes & fees

25 Oct - 26 Oct

A two-story house with a white picket fence, a blue door, and a porch with white railings.

A dining area with floral tablecloths, white chairs, and a wooden floor.

A two-story house with a white picket fence, a porch with outdoor furniture, and a mailbox.

A living room with a sofa, two armchairs, a glass coffee table, and a rug.

11. An English Garden Bed & Breakfast

Dennis Port

Pamela

฿6,455

฿8,347 total

includes taxes & fees

6 Nov - 7 Nov

A room with nautical-themed decor, including a map, anchor-patterned rug, and a view of the sea through the window.

A hotel room with a bed, two nightstands, a chair, a fireplace, and wall art.

A blue outdoor seating area with picnic tables and umbrellas, surrounded by a wooden fence and trees.

A clear blue swimming pool with a metal ladder, surrounded by lounge chairs and an American flag.

12. A Beach Breeze Inn

West Harwich

Debra

฿4,325

฿4,950 total

includes taxes & fees

13 Oct - 14 Oct

A spacious living room with a large abstract painting, two chandeliers, and a coffee machine.

A dining area with a Monopoly board game, patterned chairs, and a large map on the wall.

A playground with two blue slides and a climbing structure.

A building with a flag, a sign, and a pathway lined with flowers.

13. Brewster Green Resort

Brewster

Margaret

฿9,626

฿11,017 total

includes taxes & fees

13 Oct - 14 Oct

A wooden deck with a table and two green chairs, overlooking a beach with a fence and a building in the background.

A hotel room with two beds, a dining table with chairs, a TV mounted on the wall, and large windows offering a view of the sea.

An aerial view of a coastal resort with a large building featuring a swimming pool, beach access, and a rocky shoreline.

A large beachfront property with a pool, outdoor seating, and a covered patio.

14. The Corsair & Cross Rip Oceanfront Resort

Dennis Port

Timothy Jon

฿3,392

฿4,167 total

includes taxes & fees

15 Oct - 16 Oct

A plate of French toast with bananas on a beach view.

A sunroom with large windows, white furniture, and a ceiling fan.

A bedroom with a view of the ocean through a window, a bedside table with a plant, and a bed with white bedding.

A bedroom with a view of the beach through a window, a small table with a plant, and a bed with white linens.

15. By the Sea Guests Bed & Breakfast & Suites

Dennis Port

Jason

฿6,122

฿7,966 total

includes taxes & fees

24 Oct - 25 Oct

A two-story building with a sign for 'Ambassador Inn & Suites'.

A hotel room with a large bed, a headboard with built-in lighting, a bedside table with a phone and a remote control, and a wall-mounted painting of a beach scene.

A reception area with a wooden counter, a red mat, and a painting of a bridge.

A hotel with a row of windows, a parking lot, and a garden with marigold flowers.

16. Ambassador Inn & Suites

Bass River

Kevin

฿3,823

฿4,661 total

includes taxes & fees

13 Oct - 14 Oct

A large, multi-story beachfront hotel with a prominent balcony and multiple windows.

A grassy area with a building in the background, a flag, and several parked cars.

A beachfront property with a large building, a sandy beach, and a rocky shoreline.

A waterfront property with outdoor seating, a long pathway, and a view of the sea.

17. Lighthouse Inn

West Dennis

Megan

฿6,005

฿6,873 total

includes taxes & fees

13 Oct - 14 Oct

An outdoor seating area with a fire feature, a pool, and a view of the ocean.

A spacious room with a large window overlooking the ocean, a stone fireplace, and a modern chandelier.

A bedroom with a large bed, two armchairs, a small table, and a view of the sea through large windows.

A pool area with lounge chairs and a table, overlooking the ocean.

18. Pelham House Resort

Dennis Port

Melinda

฿8,684

฿10,933 total

includes taxes & fees

25 Oct - 26 Oct

A hotel with a white facade, a covered outdoor seating area with white chairs and tables, and a view of the sunset.

A spacious dining area with white chairs and a marble table, a staircase, and a TV in the background.

A two-story building with a white picket fence, a 'No Lifeguard on Duty' sign, and a 'Shallow Water No Diving' warning sign.

A nighttime pool area with lounge chairs and a lifebuoy.

19. The Escape Inn

Bass River

Toby

฿3,010

฿3,445 total

includes taxes & fees

1 Nov - 2 Nov

An outdoor patio with tables and chairs, umbrellas, and a view of the ocean.

A restaurant with brick arches, wooden tables, and chairs. There is a bar area with bottles and a television screen.

A golf course with sand bunkers, trees, and a clear blue sky.

Three children playing in shallow water on a beach.

20. The Villages at Ocean Edge

Brewster

Myunghee

฿3,363

฿5,384 total

includes taxes & fees

8 Nov - 9 Nov

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Stay near popular South Chatham attractions

Forest Beach

9.6/10 (13 reviews)

Forest Beach offers tranquil shores and calm waters perfect for family swimming along Nantucket Sound. Collect seashells at dawn or try windsurfing in the afternoon breeze away from Cape Cod's busier beaches.

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Learn more about South Chatham

Peaceful Pleasant Bay invites kayakers to paddle alongside seals while Ridgevale Beach offers perfect sandcastle-building at low tide. Nearby Chatham's lighthouse and Main Street shops make excellent half-day excursions when you're ready for more activity.

See all hotels in South Chatham

An aerial view of a coastal area with a large bay, sandy beaches, and a distant cityscape.

Top South Chatham Hotel Reviews

Hyannis Travel Inn

8/10 Good

"Although dated, the Hyannis Travel Inn was very clean and the rooms were serviced every day. The staff was exceptionally friendly and helpful and the location of the hotel was ideal (close to ferries and Main Street). The breakfast was satisfactory. We would definitely stay here again!"

Cape Cod Family Resort and Parks

10/10 Excellent

"Excellent experience"

Lighthouse Inn

8/10 Good

"Beautiful property, view of the ocean. Fireplace is very nice amenity."

Chatham Tides

10/10 Excellent

"Beautiful ocean views, clean room with comfortable bed and bedding. Staff was welcoming and helpful. Location was convenient and safe. Would stay here again."

Sunbird Cape Cod Resort

10/10 Excellent

"Property was clean and staff were very friendly."

Hyannis Harbor Hotel

8/10 Good

"It was a nice property to stay at the sum of the locks. Didn't work at the door you had coffee in the morning, but no breakfast. Available"

Holiday Inn Express Hyannis Cape Cod by IHG

10/10 Excellent

"The breakfast, the potatos could of been more seasoned"

Red Jacket Beach Resort

10/10 Excellent

"Beautiful river views. Staff were very nice and helpful."

More cheap stays in South Chatham

GuestLodge

221 Main Street West Dennis MA

฿2,364

฿2,705 total

16 Oct - 17 Oct

includes taxes & fees

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA

฿2,434

฿2,786 total

15 Oct - 16 Oct

includes taxes & fees

Hyannis Travel Inn

18 North St Hyannis MA

฿3,319

฿3,799 total

13 Oct - 14 Oct

includes taxes & fees

9.6/10 Exceptional! (1,013 reviews)

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA

฿3,387

฿3,876 total

29 Oct - 30 Oct

includes taxes & fees

8.8/10 Excellent! (132 reviews)

Hyannis Plaza Hotel

662 Main Street Hyannis MA

฿3,520

฿4,364 total

16 Oct - 17 Oct

includes taxes & fees

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA

Get rates

8.4/10 Very good! (1,002 reviews)

Frequently asked questions

What's the best place for a stay in South Chatham?

Based on Expedia's traveller preferences, Chatham Tides is a top place to stay in South Chatham. Other good choices for your trip to the area are Margaritaville Resort Cape Cod and Bayside Resort Hotel. See all available top hotels, or vacation rentals in South Chatham.

If I need to cancel my hotel reservation in South Chatham, will I receive a refund?

Yes, the majority of hotel room reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in South Chatham.

What are some accommodation options with pools in South Chatham?

Margaritaville Resort Cape Cod: Resort located near Hyannis Harbor. Offers a children's pool, an indoor pool and a water park. Bayside Resort Hotel and Uncommoner Hotel by Reverie Boutique Collection are two additional hotels that feature an on-site pool. View all hotels with pools in South Chatham.

What's it like to stay in South Chatham?

Visitors to South Chatham will definitely enjoy the beaches. Tourists can also enjoy the city's seafood restaurants and forests. In South Chatham, there are 111 hotels and other accommodation options to choose from. Find out more about South Chatham.

What is there to see in South Chatham?

Natural beauty is on display at Cape Cod Beaches, Forest Beach and Cockle Cove Beach. Additionally, you might want to add Chatham Chamber of Commerce to your itinerary. Take a look at what more there is to see and do in Expedia's South Chatham guide.

What's the seasonal weather in South Chatham?

The hottest months are usually August and July, with an average temperature of 19°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for South Chatham is 1362 mm.

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Book Hotels in South Chatham on Expedia.com

Find hotels in South Chatham, MA from ฿2,705

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in South Chatham

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for South Chatham hotels

1. Chatham Tides

2. Chatham Seafarer Inn

3. Handkerchief Shoals Inn

4. Pleasant Bay Village Resort

5. Chatham Wayside Inn

6. Greyfinch Chatham Inn

7. Kingfisher Harwich Port

8. Winstead Inn

9. Pelham on Earle

10. The Hawthorne

11. An English Garden Bed & Breakfast

12. A Beach Breeze Inn

13. Brewster Green Resort

14. The Corsair & Cross Rip Oceanfront Resort

15. By the Sea Guests Bed & Breakfast & Suites

16. Ambassador Inn & Suites

17. Lighthouse Inn

18. Pelham House Resort

19. The Escape Inn

20. The Villages at Ocean Edge

Stay near popular South Chatham attractions

Forest Beach

Learn more about South Chatham

Top South Chatham Hotel Reviews

Hyannis Travel Inn

Cape Cod Family Resort and Parks

Lighthouse Inn

Chatham Tides

Sunbird Cape Cod Resort

Hyannis Harbor Hotel

Holiday Inn Express Hyannis Cape Cod by IHG

Red Jacket Beach Resort

More cheap stays in South Chatham

GuestLodge

Cape Sands Inn

Hyannis Travel Inn

Holiday Inn Express Hyannis Cape Cod by IHG

Hyannis Plaza Hotel

Holiday Hill Inn & Suites

Frequently asked questions

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