Chatham

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$300

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Pondside - Water Views and a Natural Quiet Setting

Chatham house
3 BR / 2 BA / Sleeps 4 | Quick view
Excellent14 Reviews

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Reviews

(14)

Pondside is a quaint and quiet nature-lover’s paradise! Close to town and beaches, this charming non-smoking home is situated on more than an acre of woodland between three picturesque kettle ponds. The house sits just fifty feet from one small pond that’s perfect for fishing and kayaking. Next door there’s a …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(14)

A thoroughly relaxing and peaceful time.

Left on Jul 28, 2010 for a stay in July 2010

The house was abundantly equipped. Bob and Danielle could not have been more helpful without being one of the party! We particularly enjoyed the location being next door to a delightful swimming pond whilst just far enough outside of Chatham centre for it to be really quiet. The house worked really well for us and our three teenagers and we have many happy memories of our week's stay.

$120

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Quiet Lakeside Cottage - Ideal for Couple

Chatham cottage
1 BR / 1 BA / Sleeps 3 | Quick view
Excellent10 Reviews

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Reviews

(10)

At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities. Enjoy beautiful sunsets as well as swimming and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage features cathedral ceilings, a fireplace in the living room, new modern kitchen…
  • Internet Access
  • Fireplace
  • A/C or climate control
  • Central heating
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(10)

A relaxing week on Cape Cod

Left on Apr 13, 2011 for a stay in September 2010

My wife and I stayed here for a week in mid September. We loved the rustic feel of it. You are tucked away by a lake and a few minutes drive and you are in Chatham town!
The cottage is well provisioned and the internet access is a bonus. Helene was most helpful and even provided a heater the next day when I mentioned the cool evenings.

$150

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Chatham Summer Rental

Chatham house
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent4 Reviews

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Reviews

(4)

Freshly painted Cape Cod home tucked just off of Route 28 near the Chatham/Harwich line. Very convenient location with a quick walk to two great restaurants and .7 mile walk to Forest Beach, and Pleasant Street Beach. House includes an open living/dining area, a first floor master bedroom and sunroom, two upstairs …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(4)

Twosome fit fine

Left on Sep 16, 2013 for a stay in September 2013

Very clean, smaller home about a 5 minute drive from quaint Chatham's main restaurant and shopping area. Kitchen and bathrooms are dated but the full interior has a fresh coat of paint and is nicely furnished. Sweet small "sun room" was a great place to read and relax in the morning. WiFi and TV are new and easy to use. Good spot for 2-6 people to stay if you want to use it as a hub to …

$986

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Luxury WaterView 5 BR w/tennis Chatham Cape Cod

Chatham house
5 BR / 4 BA / Sleeps 10 | Quick view
Excellent11 Reviews

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Reviews

(11)

Located on a bluff overlooking Nantucket Sound just a 4 minute walk from Chatham's Hardings Beach, this luxurious home can accommodate an extended family of 10. There are two master suites with Queen beds and private bath (0ne with jacuzzi tub) and three twin bedded rooms - a total of 5 bedrooms and 3 1/2 baths plus …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(11)

Breathtaking ocean and river views

Left on May 16, 2011 for a stay in April 2010

Service was excellent and fast.

The home was luxurious, perfectly appointed, yet comfortable. Magnificent views from the expansive deck and almost every room.

Riverfront location, walk to Hardings Beach. House is fairly new, with sparkling kitchen and baths.

Liked it best for all of the above. There is nothing to dislike.

$290

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CAPE COD CHATHAM CHARMER: 2 MIN. TO THE BEACH!

Chatham house
3 BR / 2 BA / Sleeps 8 | Quick view
Very Good3 Reviews

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Reviews

(3)

Our Pleasant Street home is a charming 3 bedroom, 2 bath year-round home which is located at 320 Pleasant Street in South Chatham and it can comfortably accommodate up to 8 people. It is only a 2 minute walk to Nantucket Sound, the warm water side of Cape Cod! There is no beach sticker required at the Pleasant …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(3)

This place is perfect!!!

Left on May 24, 2012 for a stay in July 2011

This home was very comfortable, clean, and homey. The kitchen was fully equipped and we loved the large private "suite" with its own bathroom at the back of the house! The large roof deck was wonderful in the evening to relax and drink wine and the gas grill in the backyard was used nightly to grill fish. This home had every amenity we needed - washer/dryer, cable TV, and was a pleasant two-…

$275

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Cape Escape! Private Setting 5' Walk to the Beach!

Chatham house
3 BR / 2 BA / Sleeps 10 | Quick view
Excellent7 Reviews

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Reviews

(7)

Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are bright and nicely appointed with your comfort in mind…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(7)

cape escape

Left on Mar 10, 2014 for a stay in August 2013

This was the perfect house for our family vacation crew of 7. Absolutely beautiful, well maintained with lots of Cape charm. The open layout leads to a huge outdoor deck overlooking the backyard gardens. Perfect for relaxing and entertaining, this house is very private at the end of a dead-end, which was super peaceful & safe for the kids. It is close to everything, a short walk to the beach. …

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$175

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QUAINT, QUIET CHATHAM HOME NEAR COCKLE COVE BEACH

Chatham house
2 BR / 2 BA / Sleeps 6 | Quick view

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Our Cranberry Way home is a charming 2 bedroom, 2 bath (one new) year-round home which is located at 47 Cranberry Way in South Chatham and it can comfortably accommodate up to 6 people. It is only 0.6/mi. to Nantucket Sound, the warm water side of Cape Cod! It is a pet-friendly home (with an additional pet deposit …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

$200

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All New Cottage in Chatham Near Hardings Beach

Chatham cottage
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent2 Reviews

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Reviews

(2)

*** EARLY SEASON SPECIAL *** Rent for 7 days (Sat-Sat) and we'll waive the $125 cleaning fee. Valid 3/29/15 - 6/27/15 Welcome to our entirely renovated 'old Cape' cottage, with a sunny, open floor plan, brand new appliances and furnishings, washer/dryer and central air. After the beach, rinse off in the private …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Perfect cottage! A must stay!

Left on May 05, 2014 for a stay in April 2014

The description did not disappoint, this cottage is just perfect!
Everything was so clean, comfortable and beautiful we didn't want to leave. There was enough space for our family of four to relax in the living room or kitchen, and everyone had their own bed. Everything was decorated beautifully and the finishes are high end, yet comfortable. We had dinner on the patio one night...it was so …

$155

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Lovely 1 BR Chatham Cottage

Chatham cottage
1 BR / 1 BA / Sleeps 5 | Quick view
Excellent4 Reviews

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Reviews

(4)

"The Barn"--a lovely rustic cottage in Chatham, MA is located in town, an easy walk to playgrounds, kid-friendly beaches, shops, baseball field (home of the Chatham Anglers), restaurants, golf course, tennis courts, bike trail, and more. Sleeps four comfortably, add a fifth person for a small fee. One bathroom …
  • Wireless Internet
  • Outdoor Dining Area
  • Parking
  • Grill
  • Freezer
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

The perfect rustic summer getaway year after year after year.

Left on Jul 08, 2012 for a stay in August 2011

I love The Barn! I can feel the stress leave my body the moment I arrive. Walk to town, walk to the beach, walk to the ball park for an evening game. Then come "home" to sit and relax, listen to the radio, and turn in for the night with a cooling ocean breeze at the window. Kids love The Barn: there's a great yard to play in, the playground is so close, there's swim lessons at nearby Oyster Pond…

$300

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Private with 2 master suites

Chatham house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent4 Reviews

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Reviews

(4)

This fully air conditioned 4 bedroom, 3 bath house on 1/2 acre lot sleeps 8 with 2 master suites! The main house has 3 bedrooms. One with a queen, one with 2 twins and one master suite with a queen. The 2nd master suite is located in a separate attached portion of the house with separate entrance. It is a large room …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(4)

Fantastic Week with Friends

Left on Jan 14, 2014 for a stay in August 2013

It was a complete pleasure to deal with the owner of this home. Gave us many great suggestions on restaurants, stores and sights to visit.
The home was beautiful and extremely comfortable. Location was great to do anything...shop, beach, restaurants and ferries to nearby Martha's Vineyard and Nantucket. Also felt like your own home for the evenings you wanted to stay home, barbecue and relax …

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$395

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CAPE COD, CHATHAM, MA. WATERFRONT, CONTEMP RANCH

Chatham house
4 BR / 3 BA / Sleeps 10 | Quick view

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ON THE WATER ... * Beautiful water views! * Back decks open to mesmerizing views of Emery Pond * Hammock and patio furniture chosen for comfort and relaxation! * Direct access to pond from backyard. * Clean swimmable pond. * Bass fishing plentiful! * Gas grill. * 2.5 Blocks from Bike trail connecting all of …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

$525

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Former Chatham Bed and Breakfast

Chatham B&B
6 BR / 5 BA / Sleeps 12 | Quick view
Excellent4 Reviews

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Reviews

(4)

This lovingly restored Greek Victorian former bed and breakfast has 6 bedrooms and 5 full baths. Sleeps 12. Local lore has it that this property was floated over from Nantucket many years ago to its present site. Amenities include a Wolf range, granite counter tops, dishwasher, 2 cable TVs (includes NESN), DVD & VCR…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(4)

Charming and cozy home away from home!

Left on Feb 21, 2012 for a stay in May 2011

As a repeat visitor to the Nantucket house, I do not know where to begin! Lovely and charming the accomodations allow one to relax and be comfortable which is exactly what a vacation is for. A quick walk to Forest Beach provides a great sunset or sunrise and of course in the middle of the day a great place to play with the family or just relax on the beach with a good book. Chatham is a …

$358

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Beautiful sunsets in Chatham!

Chatham house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent1 Reviews

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Reviews

(1)

Enjoy this spacious home on the Monomoy River with glimpses of Pleasant Bay. Recently renovated, our home boasts a gourmet kitchen with granite counters, 6 burner Wolf cooktop and Sub Zero refrigerator and wine frig . The kitchen opens to a deck perfect for al fresco dinners watching the sunset. Gas grill is connected…
  • Ocean or water views
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

A beautiful home- wonderful attention to detail

Left on Aug 02, 2014 for a stay in July 2014

I had never used "Flip Key" before and was a bit unsure of results. I have to say that this house was perfection! From my first contact with the owner to the day we walked out the door everything was wonderful. No detail was over looked when this house was built, The deck was perfect for breakfast,lunch, and dinner. Bedrooms were perfect and the kitchen is a cooks dream! All of this made for a …

$558

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Chatham lux 5 bedrm Near bike path. Walk to pond

Chatham house
5 BR / 3 BA / Sleeps 10 | Quick view
Excellent4 Reviews

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Reviews

(4)

------------------------------------------------------------------------------------------------------ Like new 5 bedroom luxury Chatham vacation home on over 1 acre. Walk to Schoolhouse pond, clean freshwater pond with beach. Near the Cape Cod paved bike path and also only a few blocks to nice town run skateboard …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(4)

Lovely break in Charming Chatham

Left on Oct 21, 2012 for a stay in October 2012

We had spent quite a few days travelling around New England and stayed at a variety of locations. For our last four nights we decided to rent a house rather than stay in more hotels and B&B.; We found this house on the web and contacted the owner to see if it was available at short notice, we travelled to the house from Vermont and Jeff met us there to show us around. It was a lovely house, in …

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$600

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5 Bedrooms in Chatham with Lake Rights!

Chatham house
5 BR / 3 BA / Sleeps 12 | Quick view

Details

Our Five bedroom Chatham vacation home is located on a quiet side street, yet near town. The five large bedrooms are added to by a den with double pull-out and a basement/play area with 2nd pull-out making it perfect for family groups, weddings, or reunions. We have 1 king bed, two queen beds, one double bed and four…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

$200

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Chatham 1 Bedroom Beachfront Old Village

Chatham house
1 BR / 1 BA / Sleeps 3 | Quick view
Excellent3 Reviews

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Reviews

(3)

Beachfront property, close to town and lighthouse. Cottage is in Chatham's Old Village.
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(3)

Wonderful Little Cottage on Mill Pond

Left on Aug 04, 2014 for a stay in July 2014

My sister and I just got back from a 2 week stay at this lovely little cottage on Mill Pond. This is a small place - but very tastefully furnished and decorated with a nice layout. The kitchen had everything we needed. We used the BBQ and outdoor dining area several times. The outdoor shower was wonderful! We loved that we were in walking distance to downtown Chatham with all the shops and …

$915

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Spectacular Waterfront Townhome - Oyster Pond #25

Chatham house
4 BR / 5 BA / Sleeps 10 | Quick view
Excellent2 Reviews

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Reviews

(2)

OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. This is a stunning four bedroom, four and a half bath spacious end-unit townhouse with spectacular views of Oyster Pond. Unit 25 is the largest condominium in the complex. …
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(2)

Stellar location for executive retreat!

Left on Oct 30, 2014 for a stay in October 2014

We chose to hold out business retreat there and all participants stated that we exceeded expectations- which is saying something because our HQ is on Costa Rica. The quality of the accommodations, intimacy of the common rooms, and tranquil surroundings all created the perfect backdrop for an excellent off site. Highly recommend.

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$200

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Chatham Wonder- La Petite Maison

Chatham house
3 BR / 1 BA / Sleeps 5 | Quick view

Details

Adorable, cozy, renovated home - new to rental market. Air conditioned for comfort and WIFI for staying connected.Equipped with blu-Ray DVD, Dish TV with Blockbuster for streamed movies. Enjoy our gourmet kitchen with stainless steel appliances, a beautiful sunny living/dining area, deck and private yard. Three …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

$1,100

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Spectacular Waterfront Home - Oyster Pond 31&32

Chatham house
4 BR / 6 BA / Sleeps 12 | Quick view
Excellent2 Reviews

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Reviews

(2)

OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible four bedroom, five and a half bathroom double end townhouse with gorgeous direct water views of Oyster Pond. Townhomes 31 and 32 are rented together and connect …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(2)

Fabulous Cape Cod (Chatham) Family Vacation

Left on Jul 17, 2014 for a stay in July 2014

The units we rented at Oyster Pond exceeded our expectations. These two units (31 & 32) were very well appointed with TVs in every room, modern appliances, comfortable furniture, gas grills on each of two patios, and a deck with spectacular views of Oyster Pond. Each of these units come equipped with washer and dryer, ironing board and iron, all linens, including beach towels, dishwasher, and …

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$185

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4 Bedroom Home On White Pond

Chatham house
4 BR / 2 BA / Sleeps 6 | Quick view

Details

This newly renovated house overlooks White Pond in Chatham and consists of 4 bedrooms and two full bathrooms. Located on the first floor is the master bedroom with king size bed, bathroom with washer/dryer, full kitchen, living room with cable television, enclosed sun porch, and screened porch. The second floor has …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly
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$371

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SWIM, FISH, or RELAX at private Home on Goose Pond

Chatham house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Swim, fish, bike or just plain relax at this comfortable retreat in Chatham. In a quiet, wooded setting, cooled by the breezes from the pond,and ceiling fans, the home's open floor plan is well suited for gathering. The first floor of this home includes the living room, dining room, well equiped kitchen with eating …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 37

$700

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Lighthouse Beach - Shore Road Oceanside Location

Chatham house
4 BR / 3 BA / Sleeps 6 | Quick view

Details

180+ photo gallery available upon e-request. This exquisitely furnished four bedroom home is located on the Ocean side of Shore Road with an easy walk to Chatham's beaches, Fish Pier, Lighthouse, town center, outdoor band concerts and fine restaurants. Just minutes walk from The Chatham Bars Inn golf and …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 6

$171

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Ocean Front Retreat

Chatham house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Cape cod home on the shores of South Chatham. The main floor constists of an eat in kitchen, living room / dining room with three picture windows, a brick fireplace, a four window reading room facing the ocean, and a full bathroom with an accessable shower. The upstairs sleeping area has a master bedroom with a …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

$458

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Lake front Vacation home on Lovers Lake in Chatham, sleeps 10!

Chatham house
4 BR / 4 BA / Sleeps 10 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

ID #LAKE110 Lake front Vacation home on Lovers Lake in Chatham in the Great Hill Neighborhood. [~]Heron Haven is a peaceful, spacious home in a dreamy lake front setting with many sought after features. This home sleeps 10 guests and boasts 4 living areas to spread out and relax. [~]Living areas include the Lake …
  • Private Beach
  • Ocean or water views
  • Deck
  • Fitness Room
  • Garage
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

An ideal Cape Cod house for an extended family

Left on Jun 16, 2014 for a stay in July 2013

Our extended family stayed here last summer. We did a lot of research to find a place suitable for three families (grandparents, parents, and kids). We did site visits for the best properties we found on line and this one was nearly ideal. Each family had a private bedroom for the parents/grandparents, and each family had their own bathroom and shower. The kitchen is huge, with plenty of room…


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