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  • Showing 1-50 of 300+
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Exceptional! 5.0/5
(8 reviews)
avg/night
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
House #679747vb
8
Viewed 25 times in the last 48 hours
avg/night
  • 4 BR
  • 3 BA
  • 2 HF BA
  • Sleeps 10
House #837823vb
3
Viewed 23 times in the last 48 hours
Exceptional! 5.0/5
(5 reviews)
avg/night
  • 4 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 6
House #3932081
5
Viewed 24 times in the last 48 hours
Excellent! 4.7/5
(6 reviews)
avg/night
  • 3 BR
  • 1 BA
  • Sleeps 8
House #568907vb
6
Viewed 36 times in the last 48 hours
Exceptional! 5.0/5
(12 reviews)
avg/night
  • 3 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 8
House #371811vb
12
Viewed 19 times in the last 48 hours
Exceptional! 5.0/5
(10 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
House #704051vb
10
Viewed 72 times in the last 48 hours
Excellent! 4.5/5
(6 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #663482vb
6
Viewed 19 times in the last 48 hours
Exceptional! 5.0/5
(5 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #840127vb
5
Viewed 47 times in the last 48 hours
Wonderful! 4.8/5
(8 reviews)
avg/night
  • 5 BR
  • 3 BA
  • Sleeps 10
House #980094
8
Viewed 28 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 11
House #911333vb
Viewed 103 times in the last 48 hours
  • 7 BR
  • 6 BA
  • Sleeps 18
House #105821
Viewed 69 times in the last 48 hours
Exceptional! 5.0/5
(7 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #372010
7
Viewed 12 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #4165995
Viewed 17 times in the last 48 hours
Exceptional! 5.0/5
(14 reviews)
avg/night
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 11
House #223906vb
14
Viewed 27 times in the last 48 hours
avg/night
  • 5 BR
  • 2 BA
  • Sleeps 10
House #415177vb
Viewed 20 times in the last 48 hours
  • 5 BR
  • 3 BA
  • Sleeps 8
House #597355vb
Viewed 9 times in the last 48 hours
Exceptional! 5.0/5
(5 reviews)
avg/night
  • 5 BR
  • 3 BA
  • 1 HF BA
  • Sleeps 10
House #293730
5
Viewed 6 times in the last 48 hours
Exceptional! 5.0/5
(6 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 5
House #293733
6
Viewed 11 times in the last 48 hours
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
House #3942407
1
Viewed 14 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 7
House #454191vb
1
Viewed 6 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 8
House #3549672
4
Viewed 26 times in the last 48 hours
Exceptional! 5.0/5
(7 reviews)
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
House #505692vb
7
Viewed 7 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 7
House #3708573
3
Viewed 19 times in the last 48 hours
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
House #182266
2
Viewed 7 times in the last 48 hours
  • 4 BR
  • 4 BA
  • Sleeps 12
House #883157vb
1
Viewed 80 times in the last 48 hours
  • 5 BR
  • Sleeps 11
House #134363
4
Viewed 6 times in the last 48 hours
avg/night
  • 6 BR
  • 3 BA
  • Sleeps 12
House #858582vb
Viewed 12 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 4
House #223892
Viewed 43 times in the last 48 hours
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
House #843514vb
Viewed 14 times in the last 48 hours
avg/night
  • 5 BR
  • 4 BA
  • Sleeps 16
House #41681vb
2
Viewed 46 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 7
House #846409vb
Viewed 14 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 7
House #81484vb
Viewed 39 times in the last 48 hours
Viewed 7 times in the last 48 hours
  • 2 BR
  • 1 BA
  • Sleeps 4
House #859100vb
3
avg/night
  • 7 BR
  • 5 BA
  • Sleeps 12
House #4459649
Viewed 10 times in the last 48 hours
Excellent! 4.5/5
(8 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
House #960479
8
Viewed 29 times in the last 48 hours
avg/night
  • 5 BR
  • 4 BA
  • Sleeps 12
House #733046vb
1
Viewed 29 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 6
House #753236vb
4
  • 4 BR
  • 2 BA
  • Sleeps 8
House #106032
  • 4 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 8
House #761276vb
1
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 10
House #845741vb
Viewed 5 times in the last 48 hours
Exceptional! 5.0/5
(8 reviews)
avg/night
  • 5 BR
  • 2 BA
  • Sleeps 10
House #283441vb
8
Viewed 25 times in the last 48 hours
avg/night
  • 2 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 6
House #151143
4
Viewed 12 times in the last 48 hours
Exceptional! 5.0/5
(9 reviews)
View details for price
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 8
House #599182vb
9
Viewed 7 times in the last 48 hours
avg/night
  • 3 BR
  • 1 BA
  • 1 HF BA
  • Sleeps 6
House #1001325vb
Viewed 20 times in the last 48 hours
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
House #467708vb
Viewed 30 times in the last 48 hours
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
House #738870vb
Viewed 13 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 1 HF BA
  • Sleeps 9
House #277295
3
Viewed 8 times in the last 48 hours
Exceptional! 5.0/5
(9 reviews)
avg/night
  • 4 BR
  • 4 BA
  • 1 HF BA
  • Sleeps 8
House #507862vb
9
Viewed 9 times in the last 48 hours
  • 4 BR
  • 2 BA
  • Sleeps 9
House #305915vb
  • 1 - 50 of 300+

Chilmark: House Rentals (1,575)

 

Recent Chilmark Reviews

Great House, Great Location, Great Experience

5 of 5
This review is definitely coming late as we stayed here last July, but my group was reminiscing about it recently, and I realized I never wrote the review. We had a terrible situation in which another VRBO listing cancelled on us 2 weeks away. Jennifer was amazing and extremely accommodating. She met us and quickly restored our faith back in VRBO. She was even kind enough to give us some fresh eggs from her chicken! In addition to that, she helped us get a pass to the coveted Lucy Vincent beach, which words cannot describe. The house itself is extremely private with a great front and back yard. The bedrooms are extremely spacious and comfortable. The deck gets a ton of sunlight and was great for playing cards and relaxing. There is a picnic table and grill out back as well which was perfect for making dinner together as a group. One of the best features to this house is hands down the outdoor shower. It is enclose but you get a peaceful view of the farmland and an amazing breeze. We even used it in the rain that's how amazing it was! There is truly only one downfall to this house and for some it might be a positive. Since the house is so private and nestled in the woods, the entrance can be a little hard to spot. It is labeled and everything, but still it manages to sneak up on you every time. We missed it a couple of times, but finally got the hang of it after a couple days. All in all, this house, the owner, and the experience was all amazing. Our misfortune actually turned out for the better thanks to this listing. We are so grateful and would recommend to anyone looking to stay in the area! Thanks again Jennifer! -Shannon
  • Submitted: Jan 23, 2017
  • Stayed: Jul 2016

True Vineyard Feel

5 of 5
Had a fantastic stay. The ocean breeze in every direction filled our senses as we relaxed on the deck with views of Menemsha Pond and beyond that the Atlantic. The windy country road up to the house was romantic and magical. The house was comfortable and open, all aspects of a true relaxed Vineyard feel. Enjoyed the beautiful surrounding beaches and took trips down island for entertainment or a dinner out. Truly a special and spiritual place that touches one’s soul.
  • Submitted: Aug 30, 2016
  • Stayed: Aug 2016

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 soap...you 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