258 Orleans Rd North Chatham, MA 02650

    $ 299 /Nightly

    5.0 Rating


    Beds 4 Baths 2.5 Sleeps 8

    Year-round, 4 Bedrooms Inside + Detached Loft, 2.5 Baths, (Sleeps 8 + depending on loft use in summer/shoulder season)
    My family and I live full time in Lexington, MA. We decided to purchase our first vacation home in Chatham, MA in 2008. While the main reason was the proximity to our home near Boston, we also realized how much Chatham reminded us of our time on Nantucket Island. Chatham has all the charm and beauty as Nantucket Island, which is where we married. This was our first purchase and because of the experience, quality of life, great memories and including the fantastic year-round vibe, we decided to purchase an additional property and begin our long-term investment in the town and surrounding area. This property with its nautical theme and original refurbished floors, will provide a unique experience for guests that want to have some privacy from the downtown crowds but also be within a mile of Chatham Harbor, Chatham Bars Inn and Downtown Chatham Center.  

    Beautiful year-round vacation home with finished hardwood floors throughout and a beautiful tile bathtub & shower off the master first floor bedroom. The kitchen has nice finished wood countertops with all the appliances. Includes year-round Heat and A/C throughout on those humid days/evenings! Two bedrooms up and two bedrooms down! (Loft for peak season use with king bed)
    Giant deck in fully fenced in backyard takes full advantage of both sun and yard area.  Spring, summer & fall seasonal ping pong table, above ground firepit, volleyball net, and fenced in hot/cold outdoor shower.

    Beach chairs (6+) and bikes (2+) Include cooler/wheels and beach trolley (other kids beach items) Huge stainless-steel grill (direct gas hookup) on backyard brick porch.  
    Spring/Summer garage loft open (no HVAC) for guest overflow or just kids that want some extra privacy!

    While Linens/Pillow Cases & Towels are NOT included – We DO provide pillows, blankets, toilet paper, paper towels, dish detergent, hand soap and laundry detergent! 

    HOWEVER Linen’s, Towels and Pillow Cases can be delivered to property and picked up at property by two established businesses that provide simple or bundled linen packages: The Furies Cape Cod Linens at www.furiescapecodlinenrentals.com OR Cape Linen Rentals at www.capelinenrentals.com  (It is ALWAYS CHEAPER to bring your own linens which are comprised of bed sheet, pillowcase and bath towel)  If you run into any problems or would like us to set up this for you we would gladly assist!  😊

    Evelyn and I (with our 3 children) live full time in Lexington, MA. We decided to purchase a vacation home in Chatham, MA because of the short access from Boston. Chatham has all the charm and beauty as Nantucket Island has which is where we married. It just so happens Chatham is so much easier to get to than Nantucket! This was our first purchase and because of the experience and the quality of life we have had vacationing in Chatham we have pursued additional properties and decided to create a business around vacation rentals that caters to families and friends that want to enjoy Chatham and the surrounding area while also staying in professional quality, clean and well stocked lodgings that are within a short distance to sightseeing and Chatham Downtown.  We look forward to providing you a well-deserved vacation or just long weekend away from the hustle and bustle of everyday life.

    Being in North Chatham and one mile north of the Chatham Bars Inn this location gives us great access to the Atlantic Ocean side beaches, Pleasant Bay and Downtown without running into any major traffic. Having a great coffee, pastry/muffin, sandwich, and ice cream (Chatham Perks) and cold beverages (Chatham Light Liquors) within a minute walking distant is a huge plus. We also have plenty of parking in the large driveway and have an irrigation system to insure green grass all thru the peak season! The reality is this property is in a fantastic location, should check off every item on your vacation list and is well maintained by professionals and family TLC. 
    The quality of the house and condition, including the fact there is a huge fenced in backyard with a large deck and room for fun outdoor activities, reading a book or just simple sun bathing is great. The firepit (portable) and all-weather table top tennis is fantastic and lots of fun! The outdoor hard lined gas grill has plenty of space to entertain with lots of grilling options for your guests. Additional benefits include year-round heat, A/C, flat screen /Comcast cable TV and HIGH-SPEED CABLE INTERNET! And don’t forget the unfinished loft above the garage has plenty of character and is a great spot for young teenagers and a fun “away” location to play games, sleep and just get some time away from the adults. We hope you enjoy your stay!.
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    Property Video


    Season Dates Weekday Weekends Weekly
    Shoulder Fall Season Sep 05 2023 - Oct 31 2023
    ( Minimum 3 Night stay)
    $ 325.00 $ 1,750.00
    Off Season Winter/Spring Nov 01 2023 - May 20 2024
    ( Minimum 2 Night stay)
    $ 299.00 $ 1,450.00
    Shoulder Spring Season May 21 2024 - Jun 04 2024
    ( Minimum 3 Night stay)
    $ 325.00 $ 1,850.00
    Summer Season Jun 05 2024 - Sep 04 2024
    ( Minimum 7 Night stay)
    $ 455.00 $ 3,190.00
    Shoulder Fall Season Sep 05 2024 - Oct 31 2024
    ( Minimum 3 Night stay)
    $ 325.00 $ 1,750.00
    Off Season Winter/Spring Nov 01 2024 - May 20 2025
    ( Minimum 2 Night stay)
    $ 299.00 $ 1,450.00
    Shoulder Spring Season May 21 2025 - Jun 04 2025
    ( Minimum 3 Night stay)
    $ 325.00 $ 1,850.00
    Summer Season Jun 05 2025 - Sep 04 2025
    ( Minimum 7 Night stay)
    $ 455.00 $ 3,190.00
    Shoulder Fall Season Sep 05 2025 - Oct 31 2025
    ( Minimum 3 Night stay)
    $ 325.00 $ 1,750.00
    Off Season Winter/Spring Nov 01 2025 - Dec 31 2025
    ( Minimum 2 Night stay)
    $ 299.00 $ 1,450.00

    Additional Information

    Chatham Rental Property 258 Orleans Road, Chatham, MA 02650 (Owners Phone #781-910-9307) 
    1. CHECK-IN TIME IS AFTER 3 P.M. EST AND CHECK-OUT IS 10:00 A.M. EST. NO Early  Check-ins
    2. This is a NON SMOKING unit.
    3. Pets are not permitted in rental units under any conditions (unless first approved by Owners)
    4. We will not rent to vacationing students or singles under 25 years of age  unless accompanied by an adult guardian or parent.

    5. DAMAGE/RESERVATION FEE- A $59 property insurance fee must be received within five (5) days of booking the reservation. The fee is NOT applied toward rent; and does not cover excessive cleaning and does not limit your liability if the following provisions are NOT met:  a. No damage is done to unit or its contents, beyond normal wear and tear.  b. No charges are incurred due to contraband, pets or collection of rents or  services rendered during the stay. c. All debris, rubbish and discards are placed in outside trash bins in SEALED plastic garbage bags, and soiled dishes are placed in the dishwasher and cleaned. d. All keys are left on the kitchen table and unit is left locked. e. All charges accrued during the stay are paid prior to departure. f. No noted items are lost or damaged. g. Windows and Doors are secured with either air conditioning unit or heating unit operating. h. NO Early check-in or late check-out. i. The renter is not evicted by the owner (or representative of the owner), or the local law enforcement. J. Any damage that is occurs maliciously or thru any illegal activities. NO SMOKING PERMITTED INSIDE PROPERTY 
    6. PAYMENT - An advance payment equal to 50% of the rental rate is required within 5 days of confirmation. The advance payment will be applied toward the room rent. Please make payments in the form of traveler's checks, bank money  orders, cashier’s checks, personal checks payable (preferred) or Pay Pal account.. Credit Cards may be accepted with proper authorization. The advance payment is not a damage deposit. The BALANCE OF RENT is due sixty (60) days before your arrival date.   

    Checks are made out to: David Grainger OR Evelyn Grainger Address: 1429 Massachusetts Avenue, Lexington, MA 02420 USA Contact Phone: 781-910-9307 PAYPAL EMAIL: david.grainger@maddash.net  
    7. CANCELLATIONS - Cancellations or changes that result in a  shortened stay, forfeit the full advance payment and damage/reservation deposit. Cancellation or early departure does not warrant any refund of rent or deposit.  HOWEVER as fair Vacation Rental Owners, we do leave a stipulation that if we get enough time to replace your rental period with another in the result you can't make it we will provide a full refund (minus a 10% service fee) - our properties are popular enough that there is a very good chance with enough notice we can replace that cancelled period.

    8. MAXIMUM OCCUPANCY- The maximum number of guests per property is  limited to eight (8) persons. An additional charge of $50.00 per person per  night for guests in excess of (8)  will be assessed unless otherwise approved by property owner (10 overnight guests on property is MAX). THIS PROPERTY REQUIRES A TWO (2) NIGHT MINIMUM STAY. 

    9. INCLUSIVE FEES - No additional fees are included in the rental rate. 

    ... Read More



    House Rules

    • non smoking only
    • children welcome
    • pets considered
    • Max. occupancy: 8


    • Quick Getaways
    • Special Small Events/Anniversaries
    • Friends
    • Couples
    • Family


    • Air Conditioning
    • Broadband Access
    • Clothes Dryer
    • Fireplace
    • Free Long Distance
    • Garage
    • Gas Fireplace
    • Hair Dryer
    • Heating
    • Internet
    • Iron & Board
    • Living Room
    • Parking
    • Parking for RV/Boat/Trailer
    • Telephone
    • Washing Machine
    • Wireless Internet


    • Coffee Maker
    • Cooking Utensils
    • Dishes & Utensils
    • Dishwasher
    • Ice Maker
    • Kitchen
    • Microwave
    • Oven
    • Pantry Items
    • Refrigerator
    • Stove
    • Toaster


    • Child's Highchair
    • Dining
    • Dining Room
    • Seating for up to 10 people outside and 8 people inside


    • 2 Bathrooms, 1 Half Bath


    • 4 Bedrooms, Sleeps 8
    • Central Heating and A/C


    • Books
    • DVD Player
    • Games
    • Satellite / Cable
    • Stereo
    • Television
    • Video Game Console


    • Bicycles
    • Deck / Patio
    • Lawn / Garden
    • Outdoor Grill
    • 2 bicycles
    • Ping Pong Table
    • Volley Ball Net


    • churches
    • cinemas
    • health/beauty spa
    • library
    • live theater
    • marina
    • museums
    • playground
    • recreation center
    • restaurants
    • synagogues
    • winery tours

    Leisure Activities

    • antiquing
    • beachcombing
    • bird watching
    • boating
    • horseshoes
    • miniature golf
    • paddle boating
    • scenic drives
    • shelling
    • shopping
    • sight seeing
    • sledding
    • walking
    • whale watching
    • wildlife viewing

    Local Services & Businesses

    • ATM/bank
    • Babysitter
    • fitness center
    • groceries
    • laundromat
    • massage therapist

    Sports & Adventure Activities

    • basketball court
    • cycling
    • deepsea fishing
    • fishing
    • freshwater fishing
    • golf
    • hiking
    • jet skiing
    • kayaking
    • mountain biking
    • pier fishing
    • sailing
    • scuba diving or snorkeling
    • snorkeling/diving
    • sound/bay fishing
    • surf fishing
    • surfing
    • swimming
    • tennis
    • water skiing
    • water tubing
    • wind-surfing



    Great House

    We had great time at this lovely house in Chatham! Lots of space.

    Karen D.

    Great Location!

    We had a sweet time in David and Evelyn's house. They were very responsive and helpful. The location was an easy drive to downtown Chatham, which had plenty of parking for our late June stay. The house was a little smaller than we thought from the pictures, but clean and lovely. Like many houses on the Cape, it's right on a main road so you can hear traffic... a day of that and we no longer noticed, though. Extra points for the convenient Netflix and Amazon account access already provided (no searching for passwords...) The kitchen was outfitted with EVERYTHING which made cooking for our group a breeze. The master bedroom and bathroom were gorgeous. The second bedroom upstairs has a day bed with a trundle, though, which may be a challenge for particularly tall people (my 5' 8" sister had no problem sleeping there.) I don't remember a picture of that room featured on the website; I think it was referred to as the other bedroom with twin beds. The main street in Chatham is wonderful, and don't miss the Friday night band concert downtown during the summer!

    Kristin A.

    Great Host!

    We really enjoyed our stay. Very nice house in a great location near downtown Chatham. The owners were very good about communicating with us. Highly recommend.

    Douglas W.

    Dream House!

    A true Cape Cod dream home. David and Evelyn could not have been more accommodating. My family throughly enjoyed our week on the Cape and my wife and I would highly recommend their home to everyone. Great fenced in back yard with volley ⚽️, badminton 🏸 , horseshoes, 🏓 ping pong, along with a great deck and brand new Weber gas grill. Enjoy , Enjoy Interior is beautiful, great master bedroom , kids enjoyed the loft.

    Michael S.

    Very Comfortable

    This gem was everything we needed. 4 comfortable bedrooms, with a beautiful master suite and needed privacy.

    Kitchen and living room was very comfortable and had plenty of space for all 8 of us. Fenced-in yard, huge deck, fire pit, gas grill with direct hook up.

    You would not know the house is right on Rt. 28, very quiet in back yard and traffic not to heavy.

    Will be returning!

    Thank you, Evelyn & David.

    Christopher R.

    Fantastic Location!

    Fantastic location! Walking distance to town, Oyster Pond and grocery/drug store. Comfortable home with gorgeous kitchen.

    Owner is on top of every need or question.

    Loved our stay there.

    Laura T.

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