Chatham Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Chatham holiday rentals

Exterior

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, (121 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
The price is HK$2,045
HK$4,717 total
includes taxes & fees
2 Jun - 3 Jun
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Fridge, microwave, oven, stovetop

Luxury Chatham Retreat. Walk to Main St & Beach

Luxury Chatham Retreat. Walk to Main St & Beach
Chatham
10.0 out of 10, Exceptional, (1 review)
"Beautiful house in a great location in Chatham! Walking distance to shops and restaurants. The house was well-stocked with everything we needed and the beds were so comfortable. We really enjoyed our stay here!"
United States
Maggie K.
Luxury Chatham Retreat. Walk to Main St & Beach
Interior

Town Center-Limited June and July Dates Still Open-2026 Total Renovation

Town Center-Limited June and July Dates Still Open-2026 Total Renovation
Chatham
The price is HK$3,244
HK$6,807 total
includes taxes & fees
16 Jun - 17 Jun
Town Center-Limited June and July Dates Still Open-2026 Total Renovation
TV, fireplace

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
9.6 out of 10, Exceptional, (102 reviews)
"We absolutely loved this house, very comfortable, well decorated and welcoming atmosphere. It was exactly what we needed for a weekend getaway. We will be back!"
United States
Margot C.
The price is HK$1,160
HK$4,597 total
includes taxes & fees
1 Jun - 2 Jun
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Terrace/patio

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Chatham
10.0 out of 10, Exceptional, (1 review)
"Lovely spot on the water!"
United States
Elizabeth T.
The price is HK$956
HK$4,009 total
includes taxes & fees
31 May - 1 Jun
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Interior

Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Chatham
10.0 out of 10, Exceptional, (18 reviews)
"Downtown Chatham Gem was perfect for our girls getaway weekend. Parked the cars and walked everywhere. The house was clean, beautifully decorated, and had everything we needed. Loved everything about it and we will definitely be back. "
United States
Claire S.
The price is HK$8,814
HK$14,849 total
includes taxes & fees
28 Jun - 29 Jun
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Interior

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is HK$1,120
HK$2,845 total
includes taxes & fees
31 May - 1 Jun
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3 bedrooms, desk

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
The price is HK$2,928
HK$6,285 total
includes taxes & fees
29 May - 30 May
Coastal Haven in West Dennis -15
Interior

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Yarmouth
The price is HK$1,410
HK$3,452 total
includes taxes & fees
1 Jun - 2 Jun
Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Beach nearby, sun-loungers

On Town Cove with salt water access! Kayaks and paddle board available for use!

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (61 reviews)
"Clean, great location. "
United States
Peter G.
The price is HK$1,058
HK$2,896 total
includes taxes & fees
1 Jun - 2 Jun
On Town Cove with salt water access! Kayaks and paddle board available for use!
Exterior

Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail

Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail
South Wellfleet
10.0 out of 10, Exceptional, (68 reviews)
"We really enjoyed the location and deck."
United States
Donald W.
The price is HK$3,079
HK$6,590 total
includes taxes & fees
5 Jun - 6 Jun
Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail
Beach nearby

Edgewood on Campground Beach/Steps to the Sand

Edgewood on Campground Beach/Steps to the Sand
Eastham
10.0 out of 10, Exceptional, (9 reviews)
"Cozy cottage right by the beach. Great area not for to restaurants and beaches. Would definitely stay again!"
United States
Melinda W.
The price is HK$1,553
HK$3,777 total
includes taxes & fees
31 May - 1 Jun
Edgewood on Campground Beach/Steps to the Sand
Beach nearby

🐚The Bay Cottage on Thumpertown Beach

🐚The Bay Cottage on Thumpertown Beach
Eastham
9.8 out of 10, Exceptional, (11 reviews)
"My group and I had another wonderful stay at the Bay Cottage! The space is sparkling clean when we arrived and the location cannot be beat. Tara is also very responsive and attentive which makes for an even better stay!"
United States
Sophia I.
The price is HK$1,158
HK$3,101 total
includes taxes & fees
1 Jun - 2 Jun
🐚The Bay Cottage on Thumpertown Beach
Exterior

Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (75 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is HK$2,468
HK$6,402 total
includes taxes & fees
29 May - 30 May
Family Cottage Close to Beach!!
Beach

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.6 out of 10, Exceptional, (113 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is HK$970
HK$2,500 total
includes taxes & fees
5 Jun - 6 Jun
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Fridge, microwave, oven, stovetop

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
Eastham
10.0 out of 10, Exceptional, (45 reviews)
"Great place, very clean. Host was accessible and accommodating. "
United States
Christopher M.
The price is HK$3,173
HK$7,738 total
includes taxes & fees
31 May - 1 Jun
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
Front of property

6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is HK$909
HK$5,400 total
includes taxes & fees
11 Jun - 12 Jun
6 Mi to Beach: Home w/ Deck in Brewster!
Property grounds

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
Harwich
10.0 out of 10, Exceptional, (113 reviews)
"The hosts were so accommodating and lovely. The property is adorable and well appointed! Would stay again 100 percent. "
United States
rachel n.
The price is HK$1,175
HK$3,076 total
includes taxes & fees
1 Jun - 2 Jun
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
Property grounds

The Breeze on Minister's Pond

The Breeze on Minister's Pond
Eastham
10.0 out of 10, Exceptional, (25 reviews)
"The Breeze is the cutest, warmest, comfiest home. We thoroughly enjoyed our stay and will definitely book again!"
United States
MelanieC
The price is HK$1,613
HK$3,702 total
includes taxes & fees
12 Jun - 13 Jun
The Breeze on Minister's Pond
Terrace/patio

Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed

Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed
Bass River
10.0 out of 10, Exceptional, (108 reviews)
"Nice quiet neighborhood but close to a lot of different attractions. The home was perfect for our needs."
United States
Ryan T.
The price is HK$2,068
HK$5,891 total
includes taxes & fees
30 May - 31 May
Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed
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 Chatham Hotel Reviews

Parker Beach Lodge

Parker Beach Lodge

8/10 Good
"Clean room. Very comfortable beds and pillows. Walking distance to public beach and fantastic restaurant. The only issue was the shower took 5-6 minutes to get warmed up. We only stayed 2 nights, so not a big deal."
Shannon 2-night trip
Posted 2 hours ago
Parker Beach Lodge

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Can I find a holiday rental in Chatham?

Yes, there are holiday rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the popular beaches and waterfront in Chatham. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Chatham has to offer?

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches: This highly rated holiday home rental in Chatham is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Chatham?

With 277 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

Cultural attractions include Gallery Antonia and Chatham Drama Guild, whereas Cape Cod Beaches and Chatham Lighthouse Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod National Seashore are other places worth a visit.

What are holiday rentals like in Chatham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chatham. Holiday rentals offer extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.