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

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

A white bicycle with brown tires parked outside a building with a wooden exterior.

1. Chatham Tides

South Chatham

Craig

฿5,419

฿6,203 total

includes taxes & fees

9 Nov - 10 Nov

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

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

An outdoor patio with white metal chairs and a table, surrounded by blooming pink trees.

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

2. Chatham Seafarer Inn

Chatham

Ian

฿7,834

฿8,965 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

฿5,995

฿6,861 total

includes taxes & fees

9 Nov - 10 Nov

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 covered porch with a lattice design, a stone pathway, and a view of a garden.

4. Pleasant Bay Village Resort

Chatham

sheila

฿7,544

฿8,634 total

includes taxes & fees

11 Oct - 12 Oct

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

A living room with wicker furniture, a fireplace, and a staircase.

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

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

5. Chatham Wayside Inn

Chatham

Ashley

฿6,025

฿8,359 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

฿5,722

฿7,781 total

includes taxes & fees

1 Nov - 2 Nov

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

A cozy living room with a fireplace, a Christmas tree, and festive decorations.

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

7. Winstead Inn

Harwich

Karen

฿9,841

฿11,263 total

includes taxes & fees

19 Oct - 20 Oct

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

A staircase with wooden steps and a white wall. There is a white sofa with a geometric pillow in the living area.

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

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

8. Kingfisher Harwich Port

Harwich Port

Marc

฿7,725

฿8,841 total

includes taxes & fees

18 Oct - 19 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

฿6,358

฿7,859 total

includes taxes & fees

8 Nov - 9 Nov

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

A coastal house with a view of the sea and beach.

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

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

10. The Hawthorne

Chatham

Richard

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

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

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

A residential building with a white picket fence, a mailbox, and a variety of flowering plants.

11. An English Garden Bed & Breakfast

Dennis Port

Pamela

฿6,477

฿8,376 total

includes taxes & fees

6 Nov - 7 Nov

A reception desk with a marble top, a wooden panel base, a desk lamp, a potted plant, and a wicker chair with a cushion.

A beverage station with a Coca-Cola machine, ice dispensers, and a variety of drink options.

A miniature golf course with two holes, a small pond, and a wooden bridge.

A hotel room with two beds, a desk, a television, and a window with curtains.

12. Holiday Hill Inn & Suites

Dennis Port

David

฿5,349

฿6,122 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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.

13. A Beach Breeze Inn

West Harwich

Debra

฿4,340

฿4,967 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

A beach house with a white exterior, two large windows, and a view of the ocean at sunset.

14. By the Sea Guests Bed & Breakfast & Suites

Dennis Port

Jason

฿6,142

฿7,992 total

includes taxes & fees

23 Oct - 24 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.

15. Brewster Green Resort

Brewster

Margaret

฿9,658

฿11,054 total

includes taxes & fees

19 Oct - 20 Oct

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

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

16. Pelham House Resort

Dennis Port

Melinda

฿8,713

฿10,969 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.

A hotel room with two beds, a view of the outdoors, and a balcony.

A traditional fireplace with a clock above it, surrounded by various decorative items and a modern refrigerator.

A dining area with round tables and chairs, floral centerpieces, and decorative wall signs.

17. Olde Tavern Motel And Inn

Orleans

Rosalie

฿4,743

฿5,429 total

includes taxes & fees

11 Oct - 12 Oct

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

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

A beachside property with a white fence, a staircase leading to a balcony, and a sandy beach.

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.

18. The Corsair & Cross Rip Oceanfront Resort

Dennis Port

Timothy Jon

฿3,488

฿4,278 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

A clear swimming pool with blue chairs and umbrellas, a building with blue shutters, and a clear sky.

19. Lighthouse Inn

West Dennis

Megan

฿6,025

฿6,896 total

includes taxes & fees

11 Oct - 12 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.

20. Ambassador Inn & Suites

Bass River

Kevin

฿4,145

฿5,030 total

includes taxes & fees

12 Oct - 13 Oct

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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.

See properties

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 Harbor Hotel

10/10 Excellent

"Wonderful place to stay and very convenient to the ferry and nearby restaurants/bars! Loved it."

Hyannis Travel Inn

10/10 Excellent

"Location was fantastic! It’s centrally located and walking distance to many restaurants and taverns in Hyannis. Everyone at the front desk was friendly. Room was spacious. Breakfast was adequate."

Holiday Inn Express Hyannis Cape Cod by IHG

8/10 Good

"Hotel was great, room was tiny, but clean and beds were comfortable. Breakfast was good."

Lighthouse Inn

8/10 Good

"The food in the restaurant was amazing and the staff were helpful. The hotel is in a nice area, and was great for exploring cape cod. The room was very small and lacked any modern amenities and was quite damp and not very pleasant. It was ok as a place to sleep but nothing more than that."

Hyannis Plaza Hotel

10/10 Excellent

"Very happy"

More cheap stays in South Chatham

GuestLodge

221 Main Street West Dennis MA

฿2,109

฿2,413 total

11 Oct - 12 Oct

includes taxes & fees

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA

฿2,442

฿2,795 total

15 Oct - 16 Oct

includes taxes & fees

Hyannis Travel Inn

18 North St Hyannis MA

฿3,330

฿3,811 total

13 Oct - 14 Oct

includes taxes & fees

9.6/10 Exceptional! (1,008 reviews)

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA

฿3,398

฿3,889 total

29 Oct - 30 Oct

includes taxes & fees

9/10 Wonderful! (124 reviews)

Hyannis Plaza Hotel

662 Main Street Hyannis MA

฿3,531

฿4,378 total

13 Oct - 14 Oct

includes taxes & fees

7.2/10 Good! (1,003 reviews)

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA

฿5,349

฿6,122 total

11 Oct - 12 Oct

includes taxes & fees

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 ฿2,413

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. Winstead Inn

8. Kingfisher Harwich Port

9. Pelham on Earle

10. The Hawthorne

11. An English Garden Bed & Breakfast

12. Holiday Hill Inn & Suites

13. A Beach Breeze Inn

14. By the Sea Guests Bed & Breakfast & Suites

15. Brewster Green Resort

16. Pelham House Resort

17. Olde Tavern Motel And Inn

18. The Corsair & Cross Rip Oceanfront Resort

19. Lighthouse Inn

20. Ambassador Inn & Suites

Stay near popular South Chatham attractions

Forest Beach

Learn more about South Chatham

Top South Chatham Hotel Reviews

Hyannis Harbor Hotel

Hyannis Travel Inn

Holiday Inn Express Hyannis Cape Cod by IHG

Lighthouse Inn

Hyannis Plaza Hotel

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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