3BR House Vacation Rental in Chilmark, Massachusetts

Vacation Rentals

Updated on Oct 19, 2019

Estate guesthouse, glorious water view, & 2 private beaches!

Located in: Chilmark
Superb fields-to-ocean-to-islands views from this charming guesthouse, on a historic Chilmark property. You'll enjoy a wealth of beach options. Squibnocket beach is only 3-minutes away. Below the house is our private, child-safe (no surf) beach on lake-like Menemsha Pond. Or enjoy key access to our 2nd private beach -- a spectacular site on the South Shore, offering both ocean surf and pond swimming.
Large bay windows bring the 10-mile view right into the house -- or savor it first-hand from chairs on the quiet, sunny front porch. Upstairs: watch sailboat races on the inland ponds from two bright bedrooms (one king, one double twin/king), and spot rabbits or deer on the estate lawn from the upstairs study (daybed). Downstairs: the sofa pulls out to a bed in the living area (and adjacent handicap-access bathroom/shower room) to accommodate a wheelchair-bound guest. Efficient kitchen, washer/dryer, internet, cable TV, music, games and library promote easy relaxation at home! In fall and winter the house is a snuggery, with warm bedding, central heat.
[Please note: our small, historic but efficient staircase may prove a bit steep for the elderly, those with infirmities, or small pets].

Make your own memories in this historic property!: Lovey's Cottage guesthouse is part of the hilltop Tower House estate, an up-island landmark for its Queen Anne, yellow-painted main house with red roof, and ball-topped tower. The property has changed hands only once since beginning as a multi-acre farm in the early 1800's. It has been in our family for over 50 years now -- and is being cared for by a third generation for whom the estate property was their great summertime home.

Be private -- or part of your own larger group. Lovey's Cottage has its own parking and front entrance through a small walled garden that gives onto the beautiful view. Carefully designed to work as a completely independent and private residence, Lovey's can also be rented together with the Tower House* (which sleeps 10, in 5 bedrooms) -- an arrangement which works very well for weddings, or large groups of friends, or a family with varying needs and ages. Lovey's can be a wonderful solution for grandparents needing separate and quiet time, for in-laws valuing their personal space, or even for a young family with children's nap-time or early-bedtime requirements.
(*Note: Find Tower House rental details at HomeAway #293370)
Enjoy the fall, or spring: Lovey's Cottage, with its central heat, is a wonderful spot to spend an off-season week, holiday, or get-away break. The rolling up-island landscape affords splendid open views, town beaches are accessible for long seaside walks, and island staffers at restaurants, attractions, and boutiques can take more time to welcome and converse with you than in their busier months. Many stores and services stay open into late fall, and re-open in early spring, so there's a 'buzz' to savor in these non-summer months!
Get the full listing »

More Vacation Rentals Near Chilmark,

VRBO.com logo

31 day minimum stay! In Town End of Road Charmer. WiFi, Screen Porch, Central AC

7 bedroom house in Chilmark, MA

Newer home in Oak Bluffs with over 3600 sq ft. This rather large house is located just a few blocks from the lagoon and within walking or biking distance of downtown shops and entertainment. There are...

Oyster Pond Farm House

4 bedroom house in Chilmark, MA

Oyster Pond Farm House 2 story, 4 bedrooms ( down stairs queen bed and full bath, upstairs 1 king bed, 4 twin beds and full bath ) all rooms are bright and cheerful, with water views. Home has full...

Spacious, Fully-Equipped Home on Private Road Close to Vineyard's Best Beaches

4 bedroom house in Chilmark, MA

This 3000 square foot, post & beam home is only 12 years old. Five stunning ocean and sound beaches are within biking distance or a short car ride of this beautiful three-story house, situated on 2...

Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound

3 bedroom house in Chilmark, MA

This charming and simple rustic shingled cottage is located in the quiet Spring Point area of Chilmark along Vineyard Sound. A full size deck extends across the rear exterior of the house, providing a...

Classic Edgartown Home

5 bedroom house in Chilmark, MA

The main house has 3 bedrooms and 3 bathrooms. Main house sleeps six. The loft above garages had 2 bedrooms, 1 bathroom and an outdoor shower. The loft sleeps additional four. There is a...

Secluded home w/great yard, deck & perfect location right by the lagoon beach!

4 bedroom house in Chilmark, MA

The Happy Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" There's a good reason this vacation rental...

Coastal Contemparary in Katama / South Beach / Edgartown / Bike Paths

4 bedroom house in Chilmark, MA

Katama House Rental Photos and Description: Enjoy The Light Filled Great Room with a wall of glass windows and doors, vaulted ceiling, and open Living and Dining areas, plus Gourmet Kitchen....


4 bedroom house in Chilmark, MA

The Loving Kindness Campus is located in West Tisbury, off a rural road with easy access to the market, mail, bank, walking trails and beaches. The spacious house is decorated simply with a neutral...

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

1 bedroom apartment in Chilmark, MA

This property is conveniently located near the center of Oak Bluffs and with many great restaurant and out door activity, all within walking distance from the property. You can also walk to different...

Katama - 4BR - 5 Min Walk To South Beach

4 bedroom house in Chilmark, MA

Recently updated and featured in Domino Magazine! https://www.domino.com/content/modern-marthas-vineyard-surfer-home-tour It features 4 bedrooms (on multiple levels, making it an ideal choice for...

MV Waterview Farm Contemporary Home , Ocean Views, next to Farm Neck Golf Club

3 bedroom house in Chilmark, MA

This recently renovated contemporary home is located on one of the Islands premier community settings; Waterview Farms. This is a quiet, wooded area near the third hole of Farm Neck Golf Course....

Lambert's Cove Bog House

2 bedroom house in Chilmark, MA

Originally built in 1890 as a house to accommodate the land's cranberry bog tenders, this quaint little cottage was upgraded to a year round home in 1980. It sits on 3/4 of an acre of secluded...


4 bedroom house in Chilmark, MA

This new home was constructed with the modern Martha’s Vineyard family in mind. Far enough up island to completely relax or explore the wonders of Chilmark and Aquinah. Close enough to get to the...

New listing! Remodeled, cute Vineyard cottage w/AC. 10 min walk to town!

3 bedroom house in Chilmark, MA

A young home nestled on a quiet lane, a mere 10 minute walk from all the charm and activities that downtown Oak Bluffs has to offer. Come experience phase one of the renovations we've made, including...

NEW Listing Marthas Vineyard - Newly Renovated Home

3 bedroom house in Chilmark, MA

Comfortable, year round, with open living space, and well located home in Vineyard Haven! 920 square foot, 3 bedroom home with backyard. Lovely, newly renovated summer home on hilltop near the heart...

NEW LISTING! Cozy in-law suite w/ entertainment - near Edgartown & the beach!

1 bedroom apartment in Chilmark, MA

Little Vineyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click "Book Now!" This adorable one-bedroom cottage in...

Spacious Clean 2 Bed, 2 Bath Condo, Pool, Edgartown. Kid friendly!

2 bedroom condo in Chilmark, MA

This spacious, clean air conditioned contemporary condominium in Edgartown is fully equipped for a great Vineyard vacation. This 2 bedroom, 2 bath condo, sleeps 5-6 has an open first floor with a...

Charming Lambert's Cove home

3 bedroom house in Chilmark, MA

Charming Lambert's Cove/West Tisbury house offers three bedrooms, two baths and an outdoor shower, tucked away on 2.1 private woodland acres, including beautiful landscaped gardens with stone walls...

Coffin Family Cottage

3 bedroom cottage in Chilmark, MA

Lovingly cared for by the same family since construction in 1934, this summer-only cottage is the perfect throwback to a simpler time on the island of Martha's Vineyard. Located in the tranquil woods...

In-Town Vineyard Haven House with Central AC, Walking Distance to Boat

3 bedroom house in Chilmark, MA

Enjoy the convenience of this three-bedroom home, right in the heart of Vineyard Haven. The house is a 1600 ft (.3 mile) walk from the Vineyard Haven Steamship Authority ferry terminal. It has...
VRBO.com logo

goodideazs, LLC is not affiliated with the authors of this post nor is it responsible for its content, the accuracy and authenticity of which should be independently verified.

About| Advertise| Terms| Privacy| Contact A Greater Town

Copyright © 2007-2018 goodideazs, LLC. All rights reserved.