Charming West Chop Retreat — Main House + Guesthouse on Private, Tree-Lined Lot

Light-Filled Vineyard Home - Walk to Beach, Town & Ferry

Welcome to our sunny Vineyard retreat! Nestled on a quiet half-acre lot just two blocks from Grove Street Beach and bordering the West Chop Woods, our property offers the best of both worlds — close to town, yet peaceful and secluded.

The main house is a bright, newly expanded 4-bedroom home perfect for families or groups of friends. With a high-ceilinged kitchen and den, house-length screened-in porch, two newly renovated upstairs bedrooms, and two cozy downstairs bedrooms, there’s plenty of space to gather — or spread out and relax. Multiple indoor and outdoor seating areas, tons of natural light, and a large backyard make this an ideal place to unwind and enjoy summer on the Vineyard.

In the fall, we open up our charming guesthouse — a separate, private space on the same property. The guesthouse is available for 6–8 weeks in the off-season and is perfect for a cozy getaway or working vacation. Details and photos of the guesthouse will be available closer to fall availability.

Highlights of the Main House:

- Bright, airy kitchen with marble countertops, stainless appliances, and island seating for 5
- Spacious screened-in porch with ample seating and a second dining table
- Four comfortable bedrooms:
- Upstairs: King bedroom + Queen bedroom with twin futon
- Downstairs: King bedroom + Twin bedroom (with washer/dryer)
- Two full bathrooms
- Large backyard for games and entertaining
- Detached outdoor shower — a Vineyard essential!
- TVs in the living room and all but one bedroom
- Cable, Wifi, beach chairs, and kids' beach toys included

What We Love:
- 15-minute walk to town, ferry, and shops — yet tucked away from the summer bustle
- The light-filled home is perfect for socializing or relaxing solo
- Mature trees, blooming garden beds, and a peaceful porch for morning coffee
- Proximity to nature: walk to Grove Street Beach, hike the West Chop Woods, or stroll to the West Chop Lighthouse

On-property parking for 3 cars.

Please note: The guesthouse is used by the owners during the summer months but is completely private and detached from the main house. In the fall, the guesthouse becomes available for short-term rental. See below for more details.


Private Guesthouse Near Beach & Woods - Walk to Town

Next to the main house is our charming guesthouse, a peaceful and private retreat available for rent in September and October. Whether you're looking for a quiet off-season getaway, a work-from-home change of scene, or a base for enjoying the island’s fall beauty, this light-filled space is a perfect fit.

The guesthouse is separate and private from the main house, with its own entrance, living space, kitchen, bathroom and bedrooms. It’s ideal for a solo traveler, couple, or small family looking for a cozy Vineyard experience.

Guesthouse Features:
- Open-concept studio-style layout with queen bed and comfy sitting area
- Fully equipped kitchenette with small fridge, microwave, toaster oven, and hot plate
- Dining/work table for four
- Private bathroom with shower
- Private patio with outdoor seating and grill
- Wifi, smart TV, and streaming services
- Off-street parking space included
- Linens, towels, and beach gear provided

In the fall, the Vineyard takes on a quieter, more relaxed energy — with farmers markets, crisp walks in the woods, and stunning sunsets over the Sound. The guesthouse gives you a front-row seat to this magical season.

We love sharing our home and are happy to offer tips on what to do, see, and eat while you're here. We hope you enjoy the magic of the Vineyard as much as we do.