check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag

Exceptional pond, sea and outer-island views, plus 2 private beaches.

6 Reviews
Bedrooms 3
Property type house
Minimum Stay 7 nights


Minimum Stay
7 nights


Chilmark House Rental Photos and Description

2.5 bedrooms, 2 bathrooms (1 handicap), sleeps 5

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 at first-hand from deep chairs on the quiet sunny front porch. Upstairs: watch sailboat races on the inland ponds from two bright, comfortable 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, or those with infirmities].

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.

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!

More Details
  • children welcome
  • non smoking only
  • pets considered
  • suitable for elderly or infirm
  • wheelchair accessible

Robert Schmidt
Member since: 2010
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
September 21, 2016
Call Owner

Guestbook comments from the owner

We had a wonderful time here. Great weather for June, and an amazing house and view!

We loved your unspoiled and gorgeous Hancock Beach...
Jun 2013
  • 1 of 10


based on 6 traveler reviews

Exceptional pond, sea and outer-island views, plus 2 private beaches.
average rating of 5.0 based on 16 reviews
Boston, Massachusetts

Picture Perfect Rental

  • 5 of 5

Our experience renting this cottage was nothing short of perfect. The views from this property are truly gorgeous, and we spent so much time simply sitting on the deck enjoying coffee and breakfast (from the General Store!) or reading in the afternoon. The beautiful landscaping, wildlife (deer, birds, butterfly, etc), water views, and serenity can not be beat.

The cottage was very comfortable for our group of 5. I am 8 months pregnant here with my husband, my older parents, and our 12 year old son. The downstairs is handicap accessible, complete with roll in shower/bathroom. One caveat: the stairs to the second floor are steep; I would consider bringing a baby gate and watching closely if traveling with small children.

The house was FULLY equipped with everything we might need; in fact, it was better stocked than most rentals we have encountered. Trash bags, toilet paper, every kitchen appliance you might need, games, books, abundance of towels, hand name it, they have thoughtfully provided it. There is a small TV in the living room and a DVD player which we enjoyed in the evening watching a family movie. There is wifi throughout the house, though I am not sure about streaming speed - we didn't really test it, and brought DVDs with us. The house had fans in the rooms, but the open windows caught wonderful breezes in the evening and we were comfortable without AC. The house was spotlessly clean; no beachy mildew smells here!

The location is not to be beat. Very close to the General Store, Lucy Vincent, Squibnocket, Menemsha, etc. We also had access to an incredible private beach accessible by key a little further down from LV. We were the only people there when we went, and it was spectacular.

The cottage is next to the main house, and the family who owns it is incredibly kind and generous. We felt lucky to rent their home. They were very responsive to my (numerous!!!) questions and made us feel so welcome in renting their home. We just learned it is booked up for all of next August and are devastated as we would return in a heartbeat.

We feel so fortunate to have spent a week at Lovey's!

  • Submitted: Aug 29, 2016
  • Stayed: Aug 2016
  • Source: HomeAway
Did you find this review helpful?
0 0

So Lovely!

  • 5 of 5

Our Sweet Spot.

Here’s what we enjoy about Lovey’s Cottage, specifically:

- Its open plan first-floor rooms: so the small house reads big. And upstairs, it sleeps up to six.

- It’s always kept clean, neat, and very comfortably furnished. Linens, towels are all stocked too.

- Its kitchen is well-equipped. Its library holds good books/games for kids (of many ages).

- The view is amazing: all the way across the pond to Menemsha fishing village, and out over the Sound.

- The sunny deck is where we spend a lot of time, hanging out, and enjoying the fabulous view.

- The 2 private beaches are a big deal for us… Lovey’s beach (fantastic for small kids), and Hancock beach (bliss, no crowds!).

- Plus 3 other public beaches only minutes from the house: Squibnocket, Lucy Vincent, and Aquinnah.

- Wonderful restaurants within a 5-10 minute drive: Outermost, Chilmark Tavern, HomePort, Beach Plum.

- A lot of nice island walking trails within close range of the house.

- Grocery stores, gas, library, community center (with kids’ programs), farm stands and fish markets all in Chilmark and nearby Menemsha.

Lovey’s Cottage is perfect for our smaller family units, and our guests, but with privacy from the Tower House, on the same property.

Coming back here year after year – these are some of the best weeks of every summer for us!

  • Submitted: Aug 22, 2016
  • Stayed: Jun 2016
  • Source: HomeAway
Did you find this review helpful?
0 0
McLean, VA

always a pleasure

  • 5 of 5

A small gem of a house, with the open plan main floor and the comfortable bedrooms upstairs. The porch is the perfect spot to entertain, with a view over the pond and a barbecue to grill the delicious fresh fish from the fish shop in Menemsha. There are lots of books and games for those days that are too foggy or rainy to go to the beach. There are nearby restaurants in Chilmark and Menemsha, and lots of local activities to check out, including the Artisan and Flea Market twice a week. The restaurant at the cliffs in Aquinnah is a great place to sit on the deck and watch the sun go down into the sea. We always look forward to coming back every summer.

  • Submitted: Aug 18, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Did you find this review helpful?
0 0

Amazing stay! Second year in a row!

  • 5 of 5

We love this cottage. Our family of four has come here for the past two years to celebrate the 4th of July. If you love the quiet solitude of Chilmark with easy access to both a pond and gated beach, you will love this rental. We may look at renting the Tower House with is the adjacent larger home. Highly recommend this property!

  • Submitted: Jul 8, 2014
  • Stayed: Jun 2014
  • Source: HomeAway
Did you find this review helpful?
0 0

Most fantastic time ever!!

  • 5 of 5

This cottage is simply gorgeous. Set away from noise, you can enjoy your own personal and extremely private vacation at Loveys Cottage. We enjoyed this stay very much and hope to come back next year. Our most savored moments, were in the late afternoon / early evening, when we would BBQ on the veranda, sip on wine and relax with the most stunning views. The house came equipped with everything that we could think of, and we felt very catered for (e.g. beach towels, hand soap, hair dryer etc.)

Our favorite day trip was to the private beach that is included in this cottage. The beach was huge ... and went as far as we could see in either direction! .. Lovely soft sand, not very busy, and having access to this, really made us feel that it was our own private vacation.

If you stay at Lovey's cottage, you also must visit Larsen's fish market ... WOW is all I can say! We ate a lot of freshly shucked oysters, mussels and lobster here. Fantastic!

This was really the best vacation that we have had in years. Very relaxing, fun, interesting, romantic, all with stunning ocean views!! WE LOVED IT.

  • Submitted: Jul 7, 2014
  • Stayed: Jun 2014
  • Source: HomeAway
Did you find this review helpful?
1 0
Saugatuck, MI USA

Lovey's Cottage, Martha's Vineyard

  • 5 of 5

Recently spent a fantastic fall weekend at Lovey's Cottage. The spectacular setting is perfectly complimented by this cozy, nicely decorated, well maintained home. Particularly liked the incredible views, privacy, and easy access to several beaches. The cottage is on the quiet side of the island, a comfortable distance from the crowds, but within easy reach of the Vineyard's charming towns, villages, restaurants and shopping.

We found the cottage to be incredibly clean, quite comfortable, and well equipped, and the owner very responsive, helpful, and pleasant to deal with.

The location of the cottage is perfect for kayaking, sailing, hiking and biking with ready access to rural roads, walking trails, and the waterfront.

We found Lovey's to be an excellent value for our vacation dollar and look forward to the opportunity to stay there again.

  • Submitted: Oct 18, 2010
  • Stayed: Oct 2010
  • Source: HomeAway
Did you find this review helpful?
25 0


Car: necessary


Rates & Availability

Chilmark House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Spring 2017
Apr 30 2017 - Jun 3 2017
7 night minimum stay
June 2017
Jun 4 2017 - Jun 24 2017
7 night minimum stay
Summer 2017
Jun 25 2017 - Sep 2 2017
7 night minimum stay
Fall 2017
Sep 3 2017 - Oct 28 2017
7 night minimum stay

Additional information about rental rates

Cleaning $200

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
Send a Message
Available arrival
Available stay (no arrival)


Chilmark House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1400 sq. ft.
Location Type:
  • Beach
  • Near The Ocean
  • Rural
  • Family
  • Romantic
  • Alarm Clock
  • Basic Soaps
  • Clothes Dryer
  • Fireplace
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Local Activities Guide
  • Local Maps
  • Paper Towels
  • Parking Off Street
  • Sofa Bed
  • Telephone
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • 4 Ring Stove
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Lobster Pot
  • Microwave
  • Oven
  • Refrigerator
  • Toaster
  • Dining Area
  • seating for 7 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , combination tub/shower , upstairs
    Bathroom 2 - toilet , shower , downstairs: handicap friendly
  • 3 Bedrooms, Sleeps 5
  • Bedroom 1 - 1 king
    Bedroom 2 - 2 twin/ single
    Bedroom 3 - 2 twin/ single
  • Bedroom #1 -- king bed with in-bed views across the ponds to Menemsha Village and the sea. Bedroom #2 -- double twins can convert to a king for a second master bedroom. Pond and sea views. Bedroom #3 -- a nautical study with comfortable twin daybed, + twin trundle if you need an extra sleeping spot. [Note: Sofabed on living room can accommodate a non-stairclimbing guest].
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Games
  • Games for Kids
  • Music Library
  • Radio
  • Satellite / Cable
  • Stereo
  • Television
  • VCR
  • Video Library
  • Beach Towels
  • Binoculars
  • Lawn / Garden
  • Outdoor Grill Gas
  • Small Cooler
  • Wood Deck
  • children welcome
  • non smoking only
  • pets considered
  • suitable for elderly or infirm
  • wheelchair accessible
  • arboretum
  • autumn foliage
  • bay/sound
  • botanical garden
  • churches
  • cinemas
  • forests
  • library
  • live theater
  • marina
  • museums
  • nude beach
  • playground
  • pond
  • recreation center
  • restaurants
  • synagogues
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • horseback riding
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • hiking
  • ice skating
  • mountain biking
  • pier fishing
  • roller blading
  • sailing
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Access to two private beaches: Beach #1 is an expansive, south shore Atlantic surf and swimming beach (access by association-key only), 10 minutes from the house, with adjacent inland pond perfect for crabbing, kayaking, sailing (bring equipment). Walk or drive to Beach #2, an intimate Menemsha Pond sandy shore ideal for children and adults alike. You can store a small sailboat or kayak on Beach #2. Within 3 miles: Several excellent restaurants, plus many good daytime eateries at Aquinnah/Gay Head, Chilmark & Menemsha. Also close: lively general store, public library and community center (scheduled summertime activities for kids and adults). Fabulous deepsea fishing, fly fishing off nearby Dogfish bar; fresh catch each day at Menemsha village, just across the pond. MV has several golf courses, countless nature preserves and long trails for walking, horseback & bike riding. Boutique shopping in 4 towns, plus movies. Fully refundable $500.00 security deposit.

Partner Offers

You might like these similar properties