Chilmark Rentals USA Massachusetts Chilmark

Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! | House in Chilmark

9.6 (32 Reviews) |   Pet Friendly   2 Bedrooms  2 Bathrooms  5 Guests  Wedding Venue
Chilmark House | Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!

What Makes Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! Perfect for Weddings

If you're seeking a romantic and picturesque wedding stay, the Estate Guesthouse with glorious water views and access to two private beaches is an ideal choice. This charming property offers a blend of privacy and community, making it perfect for both intimate celebrations and larger gatherings.

  • Stunning Coastal Scenery: Enjoy superb fields-to-ocean-to-islands views that provide a breathtaking backdrop for your wedding photos and memorable moments.
  • Private Beach Access: With two private beach options, including a child-safe beach on Menemsha Pond and a South Shore site, you can create unique seaside experiences for your guests.
  • Spacious Accommodations: The guesthouse features a well-designed layout with multiple sleeping arrangements, including an accessible living area, which makes it suitable for wedding parties of different sizes and needs.
  • Historic Charm: Nestled within a historic estate that has been cherished by the same family for over 50 years, you'll find the perfect romantic ambiance to celebrate your love story.
  • Easy Planning: Rent Lovey's Cottage independently or in conjunction with the adjacent Tower House to accommodate larger groups, ensuring everyone has space and comfort during your wedding getaway.

style

House

Guest Capacity

5 Guests

Services

Child Friendly, Internet, Parking

 
Chilmark, 02535, USA

Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches! - The Perfect Wedding Accommodation

Welcome to the Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!, where stunning vistas and serene surroundings create a dreamlike ambiance for your special day. This charming guesthouse, nestled on a historic property in Chilmark, Massachusetts, offers an idyllic retreat for couples looking to celebrate their wedding in a picturesque setting. With ample space for both intimate gatherings and larger celebrations, this venue is designed to cater to your every need, ensuring that your wedding memories will be cherished forever.

The Estate Guesthouse boasts an array of impressive amenities, including large bay windows that flood the living spaces with natural light and allow you to take in the breathtaking 10-mile views. Enjoy access to two private beaches, perfect for pre-wedding photos or a relaxing day by the water. The layout features two bright upstairs bedrooms (one king, one double twin/king), and a cozy living area complete with a pull-out sofa bed and accessible bathroom. Your guests will appreciate the efficient kitchen, library, and entertainment options such as internet and cable TV, making it easy to unwind after a day of festivities.

Located just minutes from the stunning Squibnocket Beach, the estate is perfectly situated for those looking to explore the beauty of Chilmark. Enjoy nearby attractions, from scenic seaside walks to local boutiques and restaurants that invite you to savor the region’s charm. The unique blend of tranquility and accessibility makes the Estate Guesthouse an ideal choice not only for weddings but also for family gatherings or weekend retreats with friends. Experience the magic of this historic property and create unforgettable moments against a backdrop of glorious water views.

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Amenities

  • Ocean view
  • Oceanfront
  • Beach access
  • Child-friendly
  • Full kitchen
  • Private beaches
  • Large bay windows
  • Front porch seating
  • Parking available
  • Living area sofa bed
  • Central heating
  • Efficient appliances
  • Wi-Fi internet
  • Cable TV
  • Games and library

Restrictions

  • Minimum check-in age: 21
  • Check-in after 4:00 pm
  • Check-out before 10:00 am
  • Extra-person charges may apply
  • Service animals exempt from fees
  • Onsite parties prohibited
  • Children welcome
  • Pet limit: 2 total
  • Special requests subject to availability
  • Government ID required at check-in

Policies

Check-in Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 21
Check-out Check-out before 10:00 am contactless check-out available
Child Policy Children are welcome.
Pet Policy 2 total pets pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Other Policy Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited property registration number c0019280620 safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

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Reviews

Andrea C. Jun 3, 2025 01:07:09 AM
Summary: Lovely Chilmark cottage with distant views to sea. Cottage is comfortable with modern conveniences yet captures MV history with a range of collectibles. Outdoor patio has comfy furniture and is a cozy spot to gather for coffee in the morning or a cocktail in the evening. A real get away.
Susan S. Sep 22, 2024 01:45:09 AM
Summary: Beautiful & clean property, with very friendly hosts! Gorgeous views! Loved it there!
Alison D. Sep 12, 2023 09:53:32 PM
Summary: The views our breathtaking! Access to the most beautiful beaches. Kitchen has everything you would want to cook in or grill out. We were able to meet the owners who are fabulous. Hidden gem with old Vineyard charm throughout the cottage.
Sara Anne B. Jun 22, 2023 04:00:16 AM
Summary: We love staying at this property! The house is cozy and has everything you need. The view and beaches are amazing. We’ve come for a few years and you can easily see the care and upgrades the owners are putting in regularly. We had a wonderful family vacation!
Mark M. Jun 1, 2023 08:32:41 PM
Summary: Excellent location. Close to several beaches. Prefer that end of the Island . Great views . Book way ahead of time very affordable. Thanks for have us . MM
Jeffrey S. Aug 3, 2022 09:52:50 PM
Summary: Our family enjoyed our time at this wonderful Chilmark cottage! The oceans views, backyard, proximity to amazing beaches, farmstands and hiking trails was amazing!
Susan S. Aug 1, 2022 07:52:22 AM
Summary: This rental actually looks great online and we were very excited to stay at Lovey's. Upon arrival, the place was old and dirty -- crumbs and dirt inside the pullout sofa, ring around the tub, rust around the basin, nasty blankets, towels and rugs oh, and yes, a mouse. The dryer was broken and the rental company said that the owners were aware and had ordered a new one -- when were they going to tell us this? Three of the five beds were lumpy and uncomfortable. There was only one beach towel for 5 people, and no beach amenities except a lame umbrella that constantly blew away. After calling the management company they were great. They came and tried as best they could to provide additional things we needed and we were allowed to use the owners dryer. Oh and one day a handyman just showed up to do some work while we were eating lunch and my daughter was showering. Pros were AMAZING views and close access to a lovely, quiet salt water pond as well as a coveted key to Hancock. Beach.
Brian R. Jul 4, 2022 06:34:10 PM
Summary: Property was great. Exactly as advertised. Wonderful views and very easy to deal with the property management. Great private beach which we really enjoyed.
Sara Anne B. Jun 12, 2022 04:46:01 PM
Summary: Our vacation couldn’t have been more perfect! The house was cozy and comfortable. The views were amazing as were the hosts/owner. The house has great touches throughout including puzzles, games, beach items - so thought! The area is wonderful. We spent a lovely family vacation at the cottage and will definitely be back!
Jon B. Jun 1, 2022 10:15:48 AM
Summary: Had a nice time at Lovey’s Cottage in Chilmark. The property was beautiful with a spectacular view of Menemsha pond. Unique historical home although could use some maintenance/upgrades to make it a 5 star property. Stairs are very steep and take some getting used to. Private beach access was an awesome perk. Hosts provided lots of useful information. Kitchen was well equipped and plenty of linens, towels, and other supplies.

Entertainment and Activities for your Chilmark guests

  • Beachcombing: Explore the stunning private beaches near Estate Guesthouse in Chilmark, Massachusetts, where you can stroll along the shore, collect seashells, and soak in the breathtaking ocean views. The serene atmosphere makes it a perfect backdrop for romantic moments before or after your wedding celebration.

  • Hiking: Discover the scenic trails of the nearby Menemsha Hills Reservation, offering panoramic vistas of Martha's Vineyard and its lush surroundings. This ideal hiking destination is perfect for couples looking to connect with nature while enjoying the tranquility that Chilmark has to offer.

  • Wine Tasting: Visit the renowned Martha's Vineyard Wine Company to sample local wines crafted from the island's unique terroir. An afternoon spent tasting exquisite wines can be an enchanting prelude to your wedding festivities at the Estate Guesthouse.

  • Boating: Experience the beauty of Chilmark from the water by renting a boat or joining a guided tour. A day on the water not only provides memorable moments but also offers stunning views of the coastline, making it a delightful addition to your wedding stay.

  • Cultural Tours: Immerse yourself in the rich history of Martha's Vineyard by exploring the charming town of Chilmark and its historic sites. These cultural experiences will add depth to your wedding adventure and create unforgettable stories to share with your guests.

  • Art Galleries: Explore local art galleries showcasing the vibrant creativity of Martha's Vineyard, where you can find unique pieces that may inspire your wedding decor. A visit to these galleries can provide a touch of inspiration for your special day, enhancing the overall atmosphere of romance and beauty.

FAQ's

Is this Chilmark house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chilmark house have a swimming pool?

No, this Chilmark house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chilmark house?

Best-rates for the Chilmark house starts from $658 per night with includes Barbecue/Outdoor Cooking, Child Friendly, Internet, Parking, View, Pet Friendly, Ocean View, Balcony/Terrace, Accessibility, Sports/Activities, Bedding/Linens, Wellness Facilities, Entertainment, TV, Oceanfront, Kitchen, Laundry, Security/Safety, Fireplace/Heating with all other amenities. Perfect for Weddings is committed to ensuring every guest experiences a comfortable and extraordinary stay, whether planning a romantic getaway, a honeymoon, a pet-friendly stay, or celebrating with the entire wedding party.

Is Chilmark house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chilmark house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chilmark house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chilmark house?

Based on the information reported by the owner or manager, the Chilmark house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chilmark house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chilmark house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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