Classifieds: Winter Rentals

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  • West Tisbury Furnished House

    Private 3bdrm /1-1/2 bath/propane heat /2 full tanks. $1450 mo + utilities, Now-May 31, 2019. 1st/last/sec /REFS. Small dog considered. 860-459-0532.

  • Edgartown Winter Rental

    1 bedroom, 1 bath, parking, W/D, Wifi available to hook up, $1000 plus utilities. Now through June 1st. Call 508-627-0510.

  • Winter Rental in Chilmark

    Available now until June 8, 2019. 3 bed rm, 2 bath. Nice deck and yard with a gas grill. Perfect for a couple. $1500 a month plus utilities. (Efficient heat and hot water). No smoking. Pets considered. First month and security deposit. Good references. Call or text 508-360-9325

  • Chilmark 3500 Sqft House

    Available mid October to mid May, enormous 4-5 BR 4 BA house off North Rd in Chilmark. Fully furnished W&D Wifi DirectTV Roku. Excellent references first last and security. Pix @ $3500 plus.


    Very private but near VH, light & airy large 2 bedroom condo w/vaulted ceiling LR, dining rm, kitchen, den w/full bath on 1st floor. 2nd floor - MB, bath & guest room w/bath. Flat screen TVs, tennis court, swimming pool. Available End of Sept-June, $1500/mo. + utilities. No pets.1st/last/security/references. 781-235-4536.

  • Oak Bluffs- House for rent

    3 bedroom/2 bath. 1st/last/security. References. No smoking, No pets. Oct. 15-May 15, 2019. $1400/mo. + Utilities. Call 508-693-9604 leave message.

  • Katama

    2 bedroom,1-1/2 bath, laundry, kitchen, dishwasher, living room, dining room, wood stove, 1-mile to beach. Now-May $600/mo. 508-627-9108/508-737-9517.

  • Oak Bluffs nr town, 3 bd 2 bth

    1 or 2 people for wonderful 3 bed 2 bath home, $1350 plus utilities. Easy walk to town. For more: info/photos, No pets/smoking. Call Joe 617 290 9640 or email

  • Walk to Lamberts Cove beach

    Beautifully furnished, fully equipped 3 bedrooms/3 bathrooms house in West Tisbury, walk to Lamberts Cove beach. Fireplace and wood stove for a cozy winter. Large garage/ storage. Separate bedroom suite with walk in shower. $1500/month + utilities Please call or text (617) 388-5645


    Furnished, 3 BR home located near Moshup Trail. Suitable for 1-2 people from October 15 through May 15. $1500 plus utilities. 508-560-5267.

  • Furnished with Water Views

    Beautifully furnished top floor two-bedroom Loft with washer and dryer in the heart of VH (main street) available for winter rental, November-May, 2019. $2200/ month cable, electricity and wifi included. Perfect for a couple, share or small family. First month and security deposit secures this gem for the season. E-mail with references to set up viewing.

  • EDGARTOWN 2 or 3 Bedrooms

    ONE 2 B/R- 1 1/2 baths, TWO 3 B/R- 2 full baths Oct.15- APR/or MAY 1 no smoking /pets $1500-$1700./mon. + utilities 508-733-0672

  • 2bed/1bath near Lagoon

    Clean, updated small house, avail mid Oct till mid May. No pets or smoking. $1700 + Text or lv msg at 781-589-3505.