Chatham Holiday Rentals, Massachusetts: Private House Rentals

A boat on a calm river, a large house with a red roof, and dense greenery in the background.

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Our top choices for Chatham hotels

A paved outdoor area with three Adirondack chairs, a street lamp, and a row of houses in the background.

A building with a blue roof, a white steeple, and a flagpole with an American flag.

A residential area with a house, a driveway, and a garden with flowering bushes.

A motel with a row of rooms, a parking lot, and a flag.

1. The Chatham Motel

Chatham

David

5.673.450 ₫

6.493.236 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

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.

A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.

2. Greyfinch Chatham Inn

Chatham

Sara

4.604.333 ₫

6.219.024 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

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

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

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.

3. Pleasant Bay Village Resort

Chatham

Allison

6.259.197 ₫

7.163.650 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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.

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

4. Chatham Seafarer Inn

Chatham

Nicholas

5.029.647 ₫

5.756.388 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A sandy beach path with wooden fencing, leading to the ocean.

A hotel room with a bed, a nightstand, a mirror, a shower area, and a lamp.

A two-story house with a covered porch, a well-maintained garden, and a driveway.

A sign for The Old Harbor Inn with a number 22 on the building.

5. Old Harbor Inn

Chatham

"Absolutely loved our stay at the inn! The whole inn is so charming and the staff (including the owners Ray and Judy) were the best!!! They serve breakfast every morning, which was so good and they also had baked goods available all day and it was also phenomenal. We were very impressed how well the property was maintained and it’s nice that the inn is slightly off of Main Street which made it quieter experience. I highly recommend this inn!"

Maria

10.281.411 ₫

11.767.031 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A pathway leading to a beach with boats in the background and a building with a tower.

An aerial view of a beach with rows of sunbeds and umbrellas, a pier extending into the water, and a small building near the beach.

A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.

6. Chatham Bars Inn

Chatham

Yousuf Hussain

13.768.937 ₫

15.758.548 ₫ total

includes taxes & fees

12 Oct - 13 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 living room with wicker furniture, a fireplace, and a staircase.

7. Chatham Wayside Inn

Chatham

Nicole Ann

9.307.154 ₫

11.779.472 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A covered porch with wicker furniture and a red cushion, a brick pathway, and a grassy area with a sign in the background.

A staircase with a wooden finish, a white wall with a teal accent, and a modern light fixture.

A dining area with a round table and white chairs, a staircase, and a blue accent wall.

A beach with people sunbathing and swimming, a rocky shoreline, and houses in the background.

8. Surfside Inn Chatham

Chatham

Jenee

6.090.730 ₫

6.970.905 ₫ total

includes taxes & fees

11 Oct - 12 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 kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".

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

9. Olde Tavern Motel And Inn

Orleans

Rosalie

2.825.062 ₫

3.233.271 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

10. Chatham Tides

South Chatham

Melissa

6.181.443 ₫

7.074.577 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

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

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.

11. Kingfisher Harwich Port

Harwich Port

Marc

5.951.550 ₫

6.811.509 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

A brick building with a white picket fence, a lawn, and a sign for Skaket Beach Motel.

A covered patio with a round table and four chairs.

A breakfast buffet with pastries, a lamp, and storage containers on a wooden table.

12. Skaket Beach Motel

Orleans

Jason

3.369.340 ₫

3.856.210 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A hotel room with two beds, a desk, a chair, a lamp, and artwork on the walls.

A wooden picnic table with a white umbrella, surrounded by greenery and a blue wall.

A reception area with a blue and white color scheme, a map on the wall, and a bookshelf filled with travel brochures.

A swimming pool with blue lounge chairs aligned along the edge.

13. GuestLodge

West Dennis

John

1.877.759 ₫

2.149.120 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

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

A bedroom with a bed, two bedside tables, a chair, a sofa, and wall art.

A compact room with a kitchenette, a dining table with four chairs, a lamp, and a painting on the wall.

14. A Beach Breeze Inn

West Harwich

Nilesh

3.343.422 ₫

3.826.534 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A garden area with a welcome sign, outdoor seating, and a blue umbrella.

A hotel room with a large bed, two bedside tables, a wall-mounted painting, and a patterned carpet.

A hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building.

15. Rodeway Inn Orleans - Cape Cod

Orleans

amanda

2.747.049 ₫

3.143.854 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

A nighttime pool area with lounge chairs and a lifebuoy.

A sign for the Escape Inn Hotel with the address 1237.

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

16. The Escape Inn

Bass River

Chad

2.428.776 ₫

2.779.706 ₫ total

includes taxes & fees

1 Oct - 2 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.

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

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

17. Handkerchief Shoals Inn

South Harwich

David

3.463.941 ₫

3.964.677 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A hotel room with a large bed, a small table with chairs, a green armchair, a dresser, and a balcony with a view of trees.

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

A row of white, two-story buildings with a white fence in front, likely a motel or small hotel.

18. Blue Rock Resort

South Yarmouth

Patricia

3.335.647 ₫

3.856.081 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A gazebo with a red roof and white trim, surrounded by a well-maintained lawn and a large tree with pink flowers.

A sandy beach with gentle waves and a clear sky.

A kitchen with a white island, a fireplace, and a surfboard decoration.

A building with a red door, black shutters, and hanging flower baskets.

19. Eagle Wing Inn - Cape Cod

Eastham

Timothy

4.380.142 ₫

5.013.060 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A multi-story hotel with balconies, a flat roof, and a clear sky.

A man sitting at a table with a laptop, overlooking a pool area with chairs and tables.

A reception area with a counter, a seated area with a lamp, and framed pictures on the wall.

A hotel room with two beds, a desk, a chair, a lamp, and a nightstand with a phone and a small table.

20. Hyannis Travel Inn

Hyannis

Anatolie

2.825.062 ₫

3.233.271 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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Stay near popular Chatham attractions

A beach with people walking and standing on the sand, and the ocean in the background.

Chatham Lighthouse Beach

9.2/10 (46 reviews)

If a restful holiday is part of your travel plans, Chatham Lighthouse Beach might be the perfect place to visit during your trip to Chatham. Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.

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A lighthouse with a glass enclosure and metal railing, set against a partly cloudy sky.

Chatham Lighthouse

9.4/10 (173 reviews)

This historic 1808 beacon stands sentinel over Cape Cod's treacherous waters, guiding mariners for generations. Join a free summer Wednesday tour to climb the 48-foot tower for panoramic Atlantic views.

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A calm sea with several boats anchored near the shore.

Chatham Fish Pier

9.4/10 (107 reviews)

Watch local fishermen unload their daily catch while seals swim nearby at this authentic working waterfront. Savour fresh seafood from the on-site market while enjoying panoramic harbour views from the observation deck.

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Chatham Windmill

9.2/10 (38 reviews)

This 1797 gristmill showcases Chatham's agricultural heritage with wooden gears and mechanisms. During summer "Corn Grinding Days," you can witness the historic mill transforming grain just as it did centuries ago.

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A beach at sunset with the sun low on the horizon, casting long shadows on the sand.

Monomoy National Wildlife Refuge

9.8/10 (14 reviews)

This coastal sanctuary provides vital habitat for migratory birds and hosts one of America's largest grey seal colonies. Explore the Morris Island Loop trail for serene harbour views and wildlife photography.

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Ridgevale Beach

9.6/10 (21 reviews)

Why not spend a care-free afternoon at Ridgevale Beach during your travels in Chatham? Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.

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Cockle Cove Beach

9.0/10 (28 reviews)

If a restful holiday is part of your travel plans, Cockle Cove Beach might be the perfect place to visit during your trip to Chatham. Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.

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Mayo House

8.0/10 (3 reviews)

Learn about the local history of Chatham with a stop at Mayo House. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

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Learn more about Chatham

Stroll the historic Main Street lined with boutiques, then head to Lighthouse Beach for seal-spotting at low tide. Seafood shacks serve the freshest catch, while the Chatham Bandstand hosts free summer concerts that locals never miss.

See all hotels in Chatham

Top Chatham Hotel Reviews

Bayside Resort Hotel

8/10 Good

"friendly staff The room is clean Good variety of breakfast (hot and cold) and they refill everything immediately if it runs out. This is one of the best breakfast offered at hotels in this price range There are also plenty of parking spots The only downside is there are some smell in corridors - probably due to the age of the hotel"

Cape Sands Inn

10/10 Excellent

"Everything was good"

Greyfinch Chatham Inn

10/10 Excellent

"It's a short walk into downtown Chatham with sidewalks provided, so no walking on side of road. Very quiet at night, and hotel met every request. One exception - electrical outlets by the side of bathroom sink did not work. A little inconvenient to find other outlets that would accommodate our electrical uses. Other than that, very nice place to stay near Chatham. Completely renovated, and very clean."

Hyannis Harbor Hotel

10/10 Excellent

"This was amazing! From the moment we walked in the lobby we felt so welcome! We booked a king room with a pullout couch for the 5 of us, 2 adults and 3 kids and the woman at the front desk asked if we would prefer 2 queen beds instead bc there was more room for the 5 of us to sleep on. We accepted and we were so grateful. The beds were so comfortable. The people are so polite, beautiful room, AMAZING location! We spent a little more than we wanted on this trip for the room but it was worth it 10000%. My daughter fell and got hurt and an employee asked was asking if she was ok. She said if you need anything please let us know. We walked back to our room and sat my daughter down and decided to call and ask the front desk if they had ice packs and someone brought ice to our room, bandaids and water bottles, and asked if we needed anything else. Staff was amazing! I felt safe here. The only thing I didnt like was that there were so many stairs. There were different levels. That was the only negative thing I have to say about this place! Will definitely be coming back!!!"

Chatham Bars Inn

10/10 Excellent

"Exceptional"

Lighthouse Inn

8/10 Good

"was good!"

Sunbird Cape Cod Resort

8/10 Good

"Good stuff everything was ok"

Pleasant Bay Village Resort

10/10 Excellent

"A wonderful place to stay in Chatham. Literally a five minute drive to the pier fish market, Main Street and the beach. Check in was easy and the staff person was very helpful in pointing out places to eat and places to go both in Chatham and nearby Orleans. The room was very clean, spacious and the turn down service was excellent. They have a great pool and hot tub. They also have a koi fish pond that is beautiful. We especially enjoyed the outdoor tables in the courtyards of each area. We were able to bring back lobster rolls from the fish market and enjoy a nice al fresco dinner. We then ran into the cleaning who offered to take our garbage from us, which was so helpful as it prevented us from stinking up the room. I would definitely recommend this resort to anyone staying n Chatham. Well worth it!"

More cheap stays in Chatham

Sunbird ANNEX Resort

226 Main St West Yarmouth MA

1.802.517 ₫

2.063.113 ₫ total

24 Sept - 25 Sept

includes taxes & fees

GuestLodge

221 Main Street West Dennis MA

1.877.759 ₫

2.149.120 ₫ total

1 Oct - 2 Oct

includes taxes & fees

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA

2.166.226 ₫

2.479.056 ₫ total

14 Sept - 15 Sept

includes taxes & fees

8.2/10 Very good! (1,148 reviews)

Hyannis Travel Inn

18 North St Hyannis MA

2.825.062 ₫

3.233.271 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Holiday Hill Inn & Suites

352 Main Street Dennis Port MA

3.084.242 ₫

3.529.915 ₫ total

14 Sept - 15 Sept

includes taxes & fees

Holiday Inn Express Hyannis Cape Cod by IHG

1470 Iyannough Road Hyannis MA

3.473.012 ₫

3.974.861 ₫ total

12 Oct - 13 Oct

includes taxes & fees

Hotels in Chatham with star rating

Frequently asked questions

What's the seasonal weather like in 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 Chatham is 1362 mm.

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Book Hotels in Chatham on Expedia.com

Find hotels in Chatham, MA from 2.063.113 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chatham

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chatham hotels

1. The Chatham Motel

2. Greyfinch Chatham Inn

3. Pleasant Bay Village Resort

4. Chatham Seafarer Inn

5. Old Harbor Inn

6. Chatham Bars Inn

7. Chatham Wayside Inn

8. Surfside Inn Chatham

9. Olde Tavern Motel And Inn

10. Chatham Tides

11. Kingfisher Harwich Port

12. Skaket Beach Motel

13. GuestLodge

14. A Beach Breeze Inn

15. Rodeway Inn Orleans - Cape Cod

16. The Escape Inn

17. Handkerchief Shoals Inn

18. Blue Rock Resort

19. Eagle Wing Inn - Cape Cod

20. Hyannis Travel Inn

Stay near popular Chatham attractions

Chatham Lighthouse Beach

Chatham Lighthouse

Chatham Fish Pier

Chatham Windmill

Monomoy National Wildlife Refuge

Ridgevale Beach

Cockle Cove Beach

Mayo House

Learn more about Chatham

Top Chatham Hotel Reviews

Bayside Resort Hotel

Cape Sands Inn

Greyfinch Chatham Inn

Hyannis Harbor Hotel

Chatham Bars Inn

Lighthouse Inn

Sunbird Cape Cod Resort

Pleasant Bay Village Resort

More cheap stays in Chatham

Sunbird ANNEX Resort

GuestLodge

Cape Sands Inn

Hyannis Travel Inn

Holiday Hill Inn & Suites

Holiday Inn Express Hyannis Cape Cod by IHG

Hotels in Chatham with star rating

Frequently asked questions

Explore a world of travel with Expedia

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