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Book Online or call HomeAway Booking Assistance 888-640-7927
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Dine at CBI on Us! Private Beach, Gorgeous Neighborhood, Lovely Cape

Bedrooms 3
Half Baths1
Space 2,200 sq. ft.
Property type house
Minimum Stay 3 - 7 nights


About the property

3 bedrooms, 2 and 1/2 baths, sleeps 7, 1 queen, 4 twins, 1 twin pullout.

BOOK A JULY WEEK BEFORE MAY 1st AND RECEIVE A $150.00 GIFT CERTIFICATE FOR DINING AT CHATHAM BARS INN!! Come for the 4th! Time to think sun, fun, good food, good friends and great times. Come enjoy easy, breezy Highwood Cottage, tucked away off N. Chatham's prettiest street. Pet friendly, too! No cleaning fee. Please read agreement for cancellation policy. This is a Saturday to Saturday rental in the summer season. Relax in the quiet calm and fresh air after a busy day of shopping downtown, away from the noise and crowds (but not too far). Sit on your beach and read while the boats glide by or play games with the kids on the expansive front lawn. This private setting is in a gorgeous estate neighborhood that is surrounded by water, perfect for those early summer morning and evening walks, with beautiful vistas everywhere. Your private beach is just a short stroll away, shared with 2 families. Bring your boat, as there's a launch area next to the beach, too! Visa / MC accepted. Returning guests enjoy a 10% discount! This is an owner-managed home. (We do not use real estate agents, so personal attention to make your vacation as enjoyable as possible is our top priority!

3 bedrooms include a queen master w/bath, walk-in closet and TV, 2 twin bedrooms, all sleeping 6 plus a twin pullout makes 7. Lovely living room, dining room seats 10-12, casual family room/kitchen and a screened porch to catch cool southerly breezes perfect for al fresco dining. Amenities include central air, wireless internet, great outdoor shower, books, games, and a wagon to transport little ones to the beach. Across the water within kayak's reach is North Beach, too. The neighborhood is surrounded by great beaches. Patio in private back yard w/ gas grill, large lawn in front for games, croquet included. Downtown is 1.8 miles past the prettiest houses in Chatham. Luxury sheets, plush towels, laundry detergent, paper goods, soaps included. No cleaning fee. Well behaved pets welcomed. We look forward to meeting you!

NEIGHBORHOOD & DOWNTOWN: 'HIGHWOOD' is located in a very exclusive neighborhood where other houses rent for twice the price w/o beach rights. It is modeled after the classic NE design of the 'Half Cape', and is well off the street for privacy and safety for children. It has very comfortable furnishings and mattresses. The backyard has a tall privacy hedge, and a large dining table, garden area and gas grill. Linger over dinner under the umbrella next to the flowers or eat out on the screened porch with candlelight to welcome the evening with family and friends. All necessities are included, such as linens, towels, laundry detergent, t.p., all kitchen gadgets,small appliances, spices, etc.. An outdoor hot and cold shower makes coming in from the beach mess-free and fun!

This section of North Chatham is the most exclusive, beautiful and quietest available, unlike the noisier, high traffic in-town area, which is still easily accessible by bike, being less than 2 miles away.

THE BEACH: Out of the driveway to the left past a handful of beautiful homes and an estate is the private beach at the end of Cotchpinicut. A wagon is provided to make transporting little ones and lunch easy. It has a new, large and sandy shallow area formed over the winter which is wonderful for children. Bring your kayak, or launch your small motor boat at the landing. The outer beach is right across the water, a quick 5 minute boat ride to the best beach in the Northeast. Great surfcasting on the ocean side, so don't forget your fishing poles!

More Details

Member since: 2007
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
April 23, 2017

About Melissa

My only concern is for the comfort of my guests. Rest assured you will have a very pleasant stay at Highwood Cottage. I started and ran a very popular shop in downtown Chatham for years called The Regatta Shop, so I have served thousands of customers on an individual basis with only the highest service in mind, always with a smile. We hope you will choose Highwood and make it your favorite summer home for years to come as others have done. Welcome!

Why Melissa chose Chatham

Location, location, location. Downtown, or the village, can be noisy. It is car exhaust-filled, and crowded everywhere. But up here, you have privacy, relaxation, fresh air, gorgeous neighborhoods and no noise or lights to keep you up at night if you don't want to be, but downtown is still easily accessible. Come visit soon! Make Highwood Cottage your own for a week, a month, as long as you want.

What makes this house unique

The property is on a very special street, as anyone in Chatham knows. That's why the properties here remain in families for generations. There just isn't a better area.


North Chatham House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2200 sq. ft.
House Rules:
  • Max. occupancy: 7
  • non smoking only ...
  • pets considered
  • children welcome
Location Type:
  • Beach
  • Near The Ocean
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Broadband Access
  • Clothes Dryer
  • Fireplace
  • Garage
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Paper Towels
  • Parking
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils ...
  • Dishwasher
  • Freezer
  • Kitchen
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining Room
  • seating for 10 people
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower
    Bathroom 2 - toilet , shower
    Bathroom 3 - toilet
    Bathroom 4 - outdoor shower
  • 3 Bedrooms, Sleeps 7
  • Bedroom 1 - 1 queen
    Bedroom 2 - 3 twin/ single , 1 sleep sofa /futon , 2 twin beds, 1 twin sleeper
    Bedroom 3 - 2 twin/ single
  • Bedroom 1 has a queen bed and bath, twin bedrooms 2 and 3 share a full bath. One twin bedroom sleeps 3 with a twin pullout and 2 twin beds. Call to confirm, location of pullout may change.
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Games
  • Games for Kids
  • Satellite / Cable
  • Television
  • Toys
  • Beach Chairs
  • Beach Towels
  • Deck / Patio
  • Golf ...
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda
  • Screen Porch / Veranda
  • Small Cooler
  • Tennis ...
  • Terrace
  • Water Sports Gear
  • 6 garden chairs
  • 4 beach chairs
  • unsuitable for elderly or infirm
  • wheelchair inaccessible
  • bay/sound
  • churches
  • cinemas
  • library
  • live theater
  • marina
  • museums
  • playground
  • pond
  • recreation center
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • eco tourism
  • horseback riding
  • scenic drives
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • groceries
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Private Beach


Wonderful! 4.9/5 -
(9 traveler reviews)

Dine at CBI on Us! Private Beach, Gorgeous Neighborhood, Lovely Cape
average rating of 4.888889 based on 9 reviews

Fantastic Spot

  • 5 of 5

Had a great stay at Highwood Cottage. The neighborhood is beautiful, great for early morning and evening walks. The house is comfortable, the yard is great for the kids and dog to play in, safe off the road. There were even fresh strawberries to pick for breakfast, too! All in all, a lovely property, we will be back.

  • Submitted: Mar 10, 2017
  • Stayed: Jul 2016
  • Source: HomeAway
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Outstanding, first class property and amenities

  • 5 of 5

Our family of 5 spent Thanksgiving week at this beautiful location. We had dinner for 12 with plenty of elbowroom. Everyone loved the first class furnishings, beautiful antiques, extremely well stocked kitchen supplies and the Bose stereo system. Beds, linens, towels all the quality you'd expect at a 5 star hotel. The owner was friendly and very helpful. Everything you would need to make your vacation perfect. This is a special location that I would highly recommend!

  • Submitted: Dec 12, 2015
  • Stayed: Nov 2015
  • Source: HomeAway
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2 0

Wonderful property and home

  • 5 of 5

My husband, toddler son and I had a fabulous vacation staying at this property. It is private yet so close to everything! The house is lovely; in fact, we have never seen a rental this nicely appointed. The kitchen is very well stocked, the house is well furnished and tastefully decorated. The beds were comfy and outdoor shower is a treat! We enjoyed eating Al fresco or on the screened porch. The house was pretty easy to toddler proof for the week, so it is good for young families. We took daily walks to the beach, Lazy Lobster, Chatham Perk and around the gorgeous neighborhood. There were little things like a broken sliding screen door and no working light in the laundry room, but these were minor in comparison to the many wonderful things about this property! We can't wait to return.

  • Submitted: Sep 23, 2015
  • Stayed: Sep 2015
  • Source: HomeAway
Owner's Response: Glad you enjoyed the property! (Both repairs are done, too, thanks!)
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2 0


  • 5 of 5

Perfect home in lovely neighborhood. The owner was a pleasure.

  • Submitted: Jul 21, 2015
  • Stayed: Jul 2015
  • Source: HomeAway
Owner's Response: Thank you so much.
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1 0

Beautiful House, Gracious Hostess!

  • 4 of 5

We actually caught Melissa and her son in the process of setting up the house for us. And the moment we walked in, it was evident that they took utmost care to ensure that the house was comfy including well stocked bathrooms, kitchen utilities, books, and board games.

The house is just a few paces away from the closest beach and better sandy beach at Shore Road is less than a 5 minute drive away. Even restaurants such as Longshore (great dinner!) and Lazy Lobster (lovely breakfast) and a few minutes driving distance from the house.

Melissa is an extremely helpful person and was always prompt in responding to mails, queries, and also took care of mailing back my phone charger that I had left back at the beach house.

All in all, I'd highly recommend Melissa's home if one wishes to experience a beautiful homestay and a gracious host!

Best wishes,

Sarthak and friends

  • Submitted: May 31, 2013
  • Stayed: May 2013
  • Source: HomeAway
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3 0

Fantastic rental for our young family

  • 5 of 5

My family stayed here for a week in mid-August for our annual family vacation on the Cape. After several summer renting properties through agencies and being somewhat disappointed I decided to try HomeAway. Best. Vacation. Yet. And we owe it in large part to this very clean, very homey rental. Our kids are still fairly small (4yo and 2yo) and we found the home stocked w anything and everything we needed to make the most of Chatham. Melissa's home is located in very quiet and peaceful North Chatham, yet near several new favorite food spots (Lazy Lobster for breakfast and Chatham Coffee Co. for our morning coffee fix) and within walking distant to a neighborhood beach that's quite private. And a very quick drive to the Orleans beaches our kids love so much (Skaket and Nauset).

Some of the amenities that made the trip so easy: quality bed linens and towels included, beach towels provided, a bin of yard toys at our disposal (the super soaker came in handy ;), very well-stocked kitchen cabinets full of pots, pans, knives, etc., a binder of restaurant menus w recommendation notes from Melissa. Plus, she stopped by to see if she could catch us to introduce herself and check on our stay.

I can't recommend this place enough. I wouldn't hesitate to rent this home again. Many many thanks Melissa!

  • Submitted: Sep 9, 2012
  • Stayed: Aug 2012
  • Source: HomeAway
Owner's Response: Thanks so much Maggie! We are so happy you all had such a great time, and thanks for the great review! Melissa
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8 1


Nearest Airport
2.5 Miles
Chatham Airport
Nearest Barpub
2 Miles
The Squire
Nearest Ferry
5 Miles
Harwich to Nantucket
Nearest Golf
1.5 Miles
Seaside Links
Nearest Motorway
5 Miles
Rte 6
Nearest Restaurant
1 Miles
Lazy Lobster
Nearest Beach
0.2 Miles
Private, Cotchpinicut
Car: recommended

Chatham offers the ultimate mix of a beautiful locale with so much to do. Book a day for saltwater fly fishing with a local captain, and eat your catch the same night. Bring a new read to the beach for the afternoon, and go out to a local playhouse for the best in summer theater in the evening. Go out for an after- theater dinner at one of the many fine restaurants in town or elsewhere on the Cape. There's an art festival on Cape Cod nearly every weekend, and we have one of the oldest existing drive-in movie theaters in the country. There are many family-friendly activities also, from pirate ship cruises to quality children's theater. Public tennis courts are a bike-ride away, as is great shopping. In essence, we've got it all for your perfect vacation.


Rates & Availability

North Chatham House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Spring 2017
Apr 1 2017 - Jun 3 2017
3 night minimum stay
Late Spring
Jun 4 2017 - Jun 23 2017
7 night minimum stay
Summer 2017
Jun 24 2017 - Aug 4 2017
Changeover Day: Saturday
7 night minimum stay
Early Fall
Sep 3 2017 - Oct 21 2017
3 night minimum stay
My Standard Rate
3 night minimum stay

Additional information about rental rates

$500.00 security deposit required. Rental fee includes cleaning.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
Enter dates for accurate pricing

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