Search Vacation Homes in Chatham

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 31 - Nov 2
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11
In four months
Feb 6 - Feb 8

Vacation Homes in Chatham

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

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

9.6 out of 10, Exceptional, (99)
"Stayed here for a weekend with my fiance and our dog and it was perfect. Short 5 minute drive from downtown and all the great restaurants and shopping. Very dog friendly with fenced in backyard. "
The price is ￥13,456
￥61,908 total
includes taxes & fees
Oct 19 - Oct 20
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Beach nearby, sun loungers

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

10.0 out of 10, Exceptional, (114)
"Comfortable and terrific location"
The price is ￥27,214
￥74,751 total
includes taxes & fees
Oct 14 - Oct 15
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
2 bedrooms, iron/ironing board, WiFi, bed sheets

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

8.6 out of 10, Excellent, (26)
The price is ￥30,238
￥79,940 total
includes taxes & fees
Oct 14 - Oct 15
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Exterior

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

4.0 star property
10.0 out of 10, Exceptional, (21)
"We had a lovely time celebrating my wife’s 60th birthday at this beautiful Chatham property. The house fit four generations perfectly, with great spaces to gather, nearby beach access, and a fun swing set for the little ones. The Chatham Bars Inn, where we ate and played tennis, is in easy walking distance. Bill, the property manager, was very responsive. "
The price is ￥200,024
￥308,005 total
includes taxes & fees
Oct 14 - Oct 15
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Fridge, microwave, oven, stovetop

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

4.0 star property
10.0 out of 10, Exceptional, (17)
The price is ￥178,102
￥294,682 total
includes taxes & fees
Oct 28 - Oct 29
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (23)
"We’d loved our stay. Great house in a great neighborhood. Would love to stay here again!"
The price is ￥15,293
￥99,176 total
includes taxes & fees
Oct 14 - Oct 15
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Sand Bar-Dog Friendly on Cooks Brook Beach
Fridge, microwave, oven, stovetop

Sand Bar-Dog Friendly on Cooks Brook Beach

10.0 out of 10, Exceptional, (19)
"Tara and Colin were amazing hosts. The house is perfect for smaller groups and the one minute walk to a gorgeous beach made for great sunsets and an overall exceptional stay! "
The price is ￥26,157
￥72,851 total
includes taxes & fees
Oct 14 - Oct 15
Sand Bar-Dog Friendly on Cooks Brook Beach
The Pet-Friendly Surf Shack Hideaway on the Cove
Smart TV, fireplace

The Pet-Friendly Surf Shack Hideaway on the Cove

10.0 out of 10, Exceptional, (20)
"Lovely property, spacious and VERY clean..location is ideal..."
The price is ￥24,999
￥77,234 total
includes taxes & fees
Oct 14 - Oct 15
The Pet-Friendly Surf Shack Hideaway on the Cove
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Outdoor dining

Sleeps 2-8/Soaking Tub/FirePit~Burrows

10.0 out of 10, Exceptional, (7)
"Overall, we had a really great stay. The home is in a quiet neighborhood & close to the beach. Everything was clean and as described in the listing. "
The price is ￥24,833
￥74,104 total
includes taxes & fees
Oct 14 - Oct 15
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Fridge, microwave, oven, stovetop

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

9.6 out of 10, Exceptional, (50)
"Enjoyed the stay at the house very much. The house was as described and very clean. Great location and we plan on staying again in the future."
The price is ￥19,957
￥78,839 total
includes taxes & fees
Oct 14 - Oct 15
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
National Seashore/Updated/Game Room~Blue Pearl
Interior

National Seashore/Updated/Game Room~Blue Pearl

10.0 out of 10, Exceptional, (8)
" We enjoyed our stay at the property. We loved the location. My only issue is two little things. First, the ppropettypropermanager is"
The price is ￥23,509
￥73,281 total
includes taxes & fees
Oct 14 - Oct 15
National Seashore/Updated/Game Room~Blue Pearl
🐚Shell City on Lt Island
Beach nearby

🐚Shell City on Lt Island

9.4 out of 10, Exceptional, (6)
"We had a perfect three night stay. The house is well appointed with comfortable beds, sheets, and towels. We used the bikes and kayaks and everything was in working order. We would gladly stay again!"
The price is ￥30,297
￥95,239 total
includes taxes & fees
Oct 14 - Oct 15
🐚Shell City on Lt Island
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
Property grounds

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

9.0 out of 10, Wonderful, (6)
"Our family stayed here for a quick Cape get away at the end of summer. The host was responsive and kind. The property was in a great location with a kitchen that had everything we needed. Great spot"
The price is ￥17,840
￥71,984 total
includes taxes & fees
Nov 11 - Nov 12
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Outdoor dining

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

10.0 out of 10, Exceptional, (172)
"Perfect spot for a few days away with the kids. The house had everything we needed and was in a great location! Would definitely rent again. "
The price is ￥13,471
￥47,259 total
includes taxes & fees
Oct 16 - Oct 17
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Pond House~Waterfront Oasis W/Jacuzzi Tub
Fridge, microwave, oven, stovetop

Pond House~Waterfront Oasis W/Jacuzzi Tub

10.0 out of 10, Exceptional, (9)
"We had a great stay at the Pond House. Everything was clean and functional. Beds were extremely comfortable! Nice spot for a two night stay."
The price is ￥23,675
￥71,566 total
includes taxes & fees
Oct 14 - Oct 15
Pond House~Waterfront Oasis W/Jacuzzi Tub
Waterfront~Dog Friendly~ Lieutenant's Lodge
On the beach

Waterfront~Dog Friendly~ Lieutenant's Lodge

10.0 out of 10, Exceptional, (10)
"Our group of 6 stayed at Lieutenant's Lodge in late May/early June -- it is such a great place. Location couldn't be more perfect - stairs down to the beach/flats right out the back door. Kitchen is great, beds and living area were super comfortable. Got stopped at the bridge once by high tide - while waiting we waded in and watched the horseshoe crabs do their thing -- very cool! We highly recommend Lieutenant's Lodge."
The price is ￥34,104
￥92,846 total
includes taxes & fees
Oct 14 - Oct 15
Waterfront~Dog Friendly~ Lieutenant's Lodge
Charming House by the Beach with Patio, Grill, FirePit
Beach nearby

Charming House by the Beach with Patio, Grill, FirePit

10.0 out of 10, Exceptional, (5)
The price is ￥19,504
￥77,865 total
includes taxes & fees
Oct 14 - Oct 15
Charming House by the Beach with Patio, Grill, FirePit
New! Sandy Point-Private beach/Dog Friendly
Fridge, microwave, oven, stovetop

New! Sandy Point-Private beach/Dog Friendly

10.0 out of 10, Exceptional, (1)
"The little touches included with this listing are what makes the difference between returning to a “house we rented” and returning to a “home away from home”. Thoughtful items like nightlights, labeled light switches (so easy but so useful), and motion sensing lights on the outdoor deck stairs for when you were out later than expected and forgot to leave the outside lights on. The kitchen is well stocked with pots, pans, and all manner of cooking gear. WiFi was super fast all throughout the...
The price is ￥32,780
￥95,311 total
includes taxes & fees
Oct 14 - Oct 15
New! Sandy Point-Private beach/Dog Friendly
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Beach nearby

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

8.4 out of 10, Very Good, (7)
"The house was fine. Great location. "
The price is ￥22,527
￥78,352 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Seaside Getaway - Harwichport Beachhouse
Beach nearby

Seaside Getaway - Harwichport Beachhouse

9.8 out of 10, Exceptional, (8)
"Great location great property"
The price is ￥30,480
￥68,801 total
includes taxes & fees
Oct 14 - Oct 15
Seaside Getaway - Harwichport Beachhouse
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"This hotel does not have an elevator. It was very difficult to get our luggage up to the 3rd floor. Not senior friendly in this respect. However, the beachside area was lovely. All in all, a good visit. "
Meme 1-night trip
Posted 3 days ago
Bayside Resort Hotel

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
474
Accommodation
2582 Vacation Homes
Lowest Price
￥47,259
Highest Price
￥308,005

Explore a world of travel with Expedia