Sunday, October 20, 2019

Classifieds: Winter Rentals

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  • Long-Term Winter Rentals

    Harbor Landing Resort in Vineyard Haven will again be welcoming long term rental over the winter months starting November 15th, 2019, until March 15th, 2020. Rooms have either two twin beds or a single king size bed and all rooms have WiFi and cable TV. Efficiency rooms have sleeping and dining areas in addition to a full kitchen. There is a large communal kitchen that is available for everyone to use, we just require that residents clean up after themselves. The monthly rent will be $900 for a Standard room, $1,300 for an Efficiency and payments may be made by credit card or check, however we will require a credit card on file for each resident. No credit hold will be taken. Please contact Ray Calloway, general manager, at 508-693-2600 or come to the hotel during Tuesday through Friday.

  • Affordable Winter Rental in OB

    Just renovated rooms with large private baths in downtown Oak Bluffs boutique hotel. Share kitchenette. Price includes weekly cleaning. $1,000/month. Call 617 906-7678 or email

  • Available now to June 6

    $950 plus utilities, first/last/security, dog ok, no smoking. Chappy, water view, three bedrooms, two baths. Text 703-472-0185.


    Two bedrooms/2 baths, furnished home, oil heat, W/D, parking, wifi available. Good references, no smoking/no pets. $2000/month plus utilities. 508-627-0514.

  • Available now until June 1

    Winter Rental in Chilmark available now until June 1, 2020. Three bedrooms, two baths. Nice deck and yard with a gas grill. Perfect for a couple. $1500/month plus utilities. (Efficient to heat). No smoking, pets considered. First month and security deposit. Call 508-360-9325 or email

  • Winter Rental

    Walk-in basement studio apartment. Fully furnished. Laundry. Available 11/1-5/1. $1300/month includes full cable/wifi, and all utilities. Call or text 508-627-0225 for more info.

  • Hotel Living this Winter

    Affordable off-season housing and extended stays now available at 227 Upper Main (the newly renovated Clarion Inn) for rates ranging from $1,600 -$2,200 per month. Enjoy all of the amenities of hotel living as a temporary home. Ideal for people in between housing or commuters looking for a comfortable, convenient space. Extended stay housing available now through mid-April. Email or call 781-433-9025 for inquiries.


    Private 3 bedrooms /1-1/2 bath/propane heat /2 full tanks. $1500 month plus utilities. Available now- May 31, 2020. Small dog possible. First/last/security/references. 860-459-0532.


    Three bedrooms, 2 baths, no smoking/no pets. Available Oct. 15 - May 31st. $1800/month plus utilities. First, last, security. Call 508-687-9933.

  • Waterfront Home

    West Tisbury private setting, great wildlife. Available November 1-April 30. Oil heat. $800/month plus utilities. No smokers. 508-560-0926.

  • One bedroom cottage and loft in Vineyard Haven

    Great and happy one bedroom cottage. Off Main Street. $1,000 plus utilities. Fully furnished, including washer and dryer, tv and WiFi. No pets. (504) 236-1981.

  • EDGARTOWN 3 Bedroom 2 Bath

    Three Bedroom/2 baths. October 15-May 1st, No smoking/pets. $1500/month plus utilities. Max 4 people. Call 508-733-0672.

  • Vineyard Haven Three bedroom 
    and separate One Bedroom

    Three plus bedroom furnished house off Main Street. Happy, great light, big yard. End of October until mid-May. $1,600 plus utilities. Separate 1 bedroom and loft guest house. $1,100 plus utilities. Please call/text (504) 236-1981.