Chatham Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Chatham Vacation Homes

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, (96)
"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 CA $285
CA $779 total
includes taxes & fees
Sep 14 - Sep 15
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham 3 Bedroom/2 Bath Retreat
Sun loungers

Chatham 3 Bedroom/2 Bath Retreat

9.0 out of 10, Wonderful, (46)
"Pam was an excellent host. The house is in a great location and served as a perfect home base for my group over 4th of July Weekend."
The price is CA $484
CA $982 total
includes taxes & fees
Sep 3 - Sep 4
Chatham 3 Bedroom/2 Bath Retreat
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, (112)
"Great location, very sweet house. Perfect for our weekend getaway."
The price is CA $415
CA $894 total
includes taxes & fees
Sep 7 - Sep 8
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
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, (19)
"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 CA $2,500
CA $3,684 total
includes taxes & fees
Sep 16 - Sep 17
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach
Outdoor dining

The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach

The price is CA $291
CA $742 total
includes taxes & fees
Sep 15 - Sep 16
The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Beach

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was perfect. Fenced in large back yard, quiet neighborhood, centrally located to everythjng. House was clean & neat neat "
The price is CA $289
CA $592 total
includes taxes & fees
Sep 5 - Sep 6
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Steps to Beaches & Main Street: Hyannis Retreat
TV, fireplace

Steps to Beaches & Main Street: Hyannis Retreat

10.0 out of 10, Exceptional, (1)
"Had a fabulous time. The rental more than exceeded our expectations! Plenty of room for 4 adults and 3 children. Loved the fire pit and the outdoor shower. Was pleasantly surprised that so many extras were included such as beach chairs, beach cart, sand toys and board games. The Kitchen was fully stocked with all the essentials. There was even a high chair if needed. The location was perfect, within walking distance to Main street and also the beach but also tucked away and private and in an...
The price is CA $126
CA $691 total
includes taxes & fees
Aug 24 - Aug 25
Steps to Beaches & Main Street: Hyannis Retreat
"Awesome Vacation while staying at "HomeAway" from Home"
Indoor pool, outdoor pool

"Awesome Vacation while staying at "HomeAway" from Home"

8.4 out of 10, Very good, (78)
"Great spot for a beach getaway!"
The price is CA $166
CA $277 total
includes taxes & fees
Sep 7 - Sep 8
"Awesome Vacation while staying at "HomeAway" from Home"
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, (16)
"We’d loved our stay. Great house in a great neighborhood. Would love to stay here again!"
The price is CA $332
CA $1,145 total
includes taxes & fees
Sep 8 - Sep 9
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Charming Cape 🌞 With Beach Pass Included, Close to Beaches and Downtown
Fridge, microwave, oven, stovetop

Charming Cape 🌞 With Beach Pass Included, Close to Beaches and Downtown

9.4 out of 10, Exceptional, (10)
"Very beautiful and clean house and yard. The house is on a busy street but backyard is quite a nice oasis."
The price is CA $325
CA $742 total
includes taxes & fees
Sep 8 - Sep 9
Charming Cape 🌞 With Beach Pass Included, Close to Beaches and Downtown
Dennis Family Retreat: Private Pool, Sauna & Beach Fun!
Pool

Dennis Family Retreat: Private Pool, Sauna & Beach Fun!

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay!The house and outdoor spaces were amazing!"
The price is CA $3,648
CA $6,237 total
includes taxes & fees
Aug 25 - Aug 26
Dennis Family Retreat: Private Pool, Sauna & Beach Fun!
The Alpine/Walk to Beach for 2 or more!
Outdoor dining

The Alpine/Walk to Beach for 2 or more!

9.0 out of 10, Wonderful, (10)
"Fifth year we vacation at the Cape.This was the beat place we had.Our host Tara was great.Always got right back to me with a response.The house was clean,it was very comfortable,and very well stocked.We will definitely stay there again."
The price is CA $551
CA $1,100 total
includes taxes & fees
Sep 12 - Sep 13
The Alpine/Walk to Beach for 2 or more!
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Outdoor dining

Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

10.0 out of 10, Exceptional, (2)
"Cosy retreat with pond view. Great for canoeing with the dog. Sweet porch for reading and morning coffee. Tara was an excellent host who communicated immediately and went well above and beyond to correct an issue that was out of her control.A great central location that allowed us to roam freely to our favorite beaches, hikes, and restaurants. We will gladly return in the future. "
The price is CA $251
CA $553 total
includes taxes & fees
Sep 1 - Sep 2
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Mariner Motor Lodge- "Where People Come By Choice And Not By Chance".
Indoor pool, a heated pool

Mariner Motor Lodge- "Where People Come By Choice And Not By Chance".

7.8 out of 10, Good, (15)
"So when I got there i had my reservation in for the day changes to a day ahead and had my email with a confirmation saying I was all set and when I got there it was never changed. Ugh! Took longer to check in and i only had so much time before wedding i was attending. Also when i told the front desk my room hair dryer didn't work i was giventhe "oh well". so that sucked"
The price is CA $166
CA $277 total
includes taxes & fees
Aug 25 - Aug 26
Mariner Motor Lodge- "Where People Come By Choice And Not By Chance".
Beach Lovers Escape
Fridge, microwave, oven, stovetop

Beach Lovers Escape

10.0 out of 10, Exceptional, (43)
"Just as advertised, lots of room for guests and great backyard area. Would definitely stay again."
The price is CA $281
CA $857 total
includes taxes & fees
Sep 5 - Sep 6
Beach Lovers Escape
Ocean Breeze Motel - Standard Double
Beach

Ocean Breeze Motel - Standard Double

9.8 out of 10, Exceptional, (50)
"Clean, comfortable hotel with good sized room and great shower. Good coffee and breakfast included with many options. Joanna, the owner was very helpful with suggestions in the area- biking, beach, sunsets, sea food restaurants. Had a great stay! "
The price is CA $220
CA $285 total
includes taxes & fees
Sep 7 - Sep 8
Ocean Breeze Motel - Standard Double
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior

Cozy Large Home in Harwich with Patio near Wequassett Resort

9.8 out of 10, Exceptional, (8)
"We had a great time here - the kids’ room is truly special!"
The price is CA $289
CA $803 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Large Home in Harwich with Patio near Wequassett Resort
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
Property grounds

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

8.6 out of 10, Excellent, (4)
"It was a quick three night trip. We enjoyed the house very much. It was just what we were looking for."
The price is CA $246
CA $766 total
includes taxes & fees
Sep 16 - Sep 17
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Outdoor dining

Sleeps 2-8/Soaking Tub/FirePit~Burrows

10.0 out of 10, Exceptional, (7)
"Very cute and comfortable 3-bedroom home. The kitchen is nice and big and very well stocked. We enjoyed the large deck."
The price is CA $480
CA $998 total
includes taxes & fees
Aug 31 - Sep 1
Sleeps 2-8/Soaking Tub/FirePit~Burrows
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, (161)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is CA $155
CA $475 total
includes taxes & fees
Aug 27 - Aug 28
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"We ended up at the Uncommoner after our VRBO was a disaster. The hotel is absolutely wonderful and uniquely designed/recently remodeled. Very well thought out and great staff! Kids loved both the indoor and outdoor pool. I loved all of the design aspects. Nearby mini golf, coffee shop, and ice cream. "
Katherine 7-night trip
Posted 1 day ago
Uncommoner Hotel by Reverie Boutique Collection