Max 6 guests 3 bedrooms 1 bath Dog-friendly 
What our guests are saying...
This is a top guest review for this property
The house was exactly what we want in a Vineyard rental— a lovely nod to how vacation homes used to be before private equity took over the market and filled everything with Amazon furnishings. Wayside is absolutely charming and in a spectacular location. It was a special visit and we are also so grateful we could bring our dog along too. Will rent again!
Genevieve M. Sep 2025
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OVERVIEW

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

Conveniently located in the center of Menemsha, steps away from restaurants, fish markets, local shops, and the beach, this two-story home offers the perfect home base for a relaxing and unforgettable vacation with your family and friends! Stop by the nearby Swordfish Harpooner Sculpture to take a memorable photo, visit any of the nearby fish markets to buy some local produce to cook later, dine at any of the quaint local restaurants, or spend the day beachcombing and sunbathing at Menemsha Public Beach. Since the beach is so close to home, feel free to use the beach chairs, umbrellas, and beach towels available. In addition, there are two kayaks if you feel like exploring the nearby pond.

This splendid home away from home features a spacious and private backyard, which makes this the ultimate quintessential Vineyard retreat! The deck offers a great spot to admire the water views of the Menemsha Channel and Vineyard Sound, dine alfresco at the outdoor dining table with an umbrella, and host summertime cookouts using the gas grill provided.

As you enter this home, you are first greeted by a cozy living room, furnished with quaint and comfortable sofas throughout and a smart TV with streaming and cable services to keep you entertained during your stay. The well-appointed, eat-in kitchen is complete with all the major appliances needed to prepare culinary masterpieces with all the local produce you have bought nearby! Attached to the kitchen is a laundry room/pantry with a washer/dryer. This level also hosts a sunny bedroom. The other two bedrooms are located upstairs, featuring partial AC window units.

THINGS TO KNOW

  • The dryer is small, so please be sure not to overload it.
  • You must be 25 years or older to rent this property.

    AMENITIES

    Features

    Iron

    Washer/dryer : Private

    Heating & cooling

    Central AC

    Partial AC

    Space heater

    House rules

    Dog-friendly

    Kitchen & dining

    Microwave

    Stove

    Location

    Water view

    Beach access

    Media

    Internet

    TV

    Cable

    On-site activities

    Kayaks

    Outdoor

    Gas grill

    Location

    Chilmark, Massachusetts, USA

    (Exact address will be provided after booking)
    Map showing the location of the Unit

    Rating

    3.73
    24 hour cancellation*
    Get a full refund if you cancel within 24 hours of booking
    Local expertise
    Count on care—just a call, text, or email away
    Lowest price
    Book directly for the lowest rates

    *Some exceptions may apply. Review the unit cancellation terms before payment.