Vacation rentals in Chappaquiddick

5 out of 5 average rating, 12 reviews

Home in Yarmouth

Gorgeous Renovation - Boat Dock, Hot Tub, 5 Beds!

RogerRating, 5 stars1 month ago

This gorgeous waterfront house is even more beautiful than the photos can capture. The views of the water from the bedrooms are particularly stunning. The living room is extremely generous and a great place to relax. Jordan and Aaron are amazing hosts--extremely friendly and very responsive. I also particularly recommend this location for the off season, since the area is peaceful and gorgeous.

4.92 out of 5 average rating, 109 reviews

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

Absolute Best Location on the Island

DanielleRating, 5 stars5 months ago

My family & I have been vacationing at Larry’s Historic Arcade for the past 7+ years. It is in the most perfect spot located right on Circuit Ave in the heart of Oak Bluffs. There are many stores and restaurants located on this road and it’s super convenient to have a market right across the street for any last minute essentials. We always rent the third floor apartment. It is very spacious and has a full size bed, a loft with 2 twin size beds and a pull out couch. It also has 2 decks. One over looking circuit ave and one on the other side with a grill. The house has WiFi, 2 mini splits (for ac or heat) a tv and a full kitchen. I highly recommend booking Larry’s Historic Arcade. It has everything you need and more. Thank you Larry for providing the perfect vacation spot for me and my family. We are already looking forward to next year!

4.94 out of 5 average rating, 110 reviews

Home in Mashpee

Newly Renovated! Seconds to sand, fire pit, A/C

EzraRating, 5 stars4 months ago

Very comfortable and cozy, in a great part of the Cape. Kitchen has all you need, good set up for a couple or even small family. One note, not a huge problem: the fireplace is only ornamental. Bed is comfortable, might be too soft for some. Very helpful and friendly host, gave clear instructions but respected privacy. Thanks so much!

4.93 out of 5 average rating, 44 reviews

Home in Mashpee

Tranquil Cape getaway#2 with AC Kid & Pet friendly

JennRating, 5 stars3 weeks ago

A wonderful spot filled with Machpee and Cape cod decor. The location was excellent given we travelled up and down the Cape and needed a spot that was centrally located. The house is well appointed and has everything you need ! It looks exactly like the photos. And the neighbourhood is very nice too.

4.9 out of 5 average rating, 48 reviews

A wooden gazebo is nestled among lush greenery, featuring an intricate design and a shingled roof. A well-maintained stone pathway, lined with soft lighting, leads through the vibrant grass and towards a backdrop of surrounding trees and a deck area.

Home in Falmouth

Cape Cod's Best Winter Getaway / Hidden Gem

KaleighRating, 5 stars5 months ago

A great house with plenty of room for everyone. The house was great and had everything we needed along with some thoughtful things a family may not want to travel with like baby items. The 2 living room areas were great to keep both adults and kids content. The hot tub was a great added bonus. A short drive to downtown area but nice and quiet neighborhood.

5 out of 5 average rating, 9 reviews

The kitchen features sleek black countertops and white cabinetry, creating a contemporary look. Stainless steel appliances, including a microwave and refrigerator, are present. A window above the sink allows natural light to illuminate the space, enhancing the overall brightness of the room.

Home in Yarmouth

Cape Escape House

SarahRating, 5 stars7 months ago

Sean’s place was just as described. We felt completely comfortable at all times. Everything was spotless upon check in. Everything we needed was there, lots of extra blankets, pillows and towels. Plenty of dishes, pots and pans, cooking utensils. Lots of nice touches to make you feel right at home. The location makes it easy to access many attractions. Thanks Sean!!

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What guests are saying

3BR Modern Home 5 Star, Walk2 Priv Beach, Mktplace

5 out of 5 average rating, 3 reviews35 months ago

Beautiful & comfortable beach house! We have stayed in a lot of short term rentals and this was definitely the best! Settled on a quiet dead end it is also directly next to a wooded path that takes you on a short walk to the Marketplace with mini golf, restaurants, and shops. It is also a short walk to the private beach. The layout of the house was perfect and it is nicely decorated as well as clean. We stayed for a long weekend with our young children to attend a wedding at the Popponesset Inn and the single level space was perfect for them. The convenience of not having to get in the car for food, beach, or activities was also priceless. Don was extremely welcoming and responded quickly with any of our questions. Would definitely stay again!

Home in Mashpee

What guests are saying

Top floor with views and steps to private beach!

4.88 out of 5 average rating, 140 reviews20 months ago

We had a wonderful stay! The space was just what our family needed for a peaceful and laid back vacation before the summer comes to a close. We enjoyed the private beach just steps away from the house, and Bob provided us with beach toys for our daughter to play with! It’s a great location to get to some local attractions! Bob was a very friendly, communicative, and helpful host!! Thank you so much for our stay, Bob!

Apartment in Bourne

What guests are saying

2BR Lakefront | Deck | Washer/Dryer

4.55 out of 5 average rating, 31 reviews11 months ago

What a great location. Yes, the pond is closer, but the Vineyard Haven Harbor is right after the pond. So the views are wonderful! We thoroughly enjoyed the deck, overlooking the water, watching and listening to the birds, and star gazing at night. Almost equally distant from "downtown" Oak Bluffs and Vineyard Haven.

Home in Oak Bluffs

What guests are saying

54 - Private forested oasis near town and beach

4.95 out of 5 average rating, 76 reviews6 months ago

We had a horrible experience with our original rental (from another app)... we couldn't stay at the original place.. with a 1 year old in tow and evening approaching, we were scampering to find a place - within 2 hrs we were checking into Clif and Lindsay's place... it saved our holiday. They were super responsive, considerate and helpful if we needed anything! Thank you Clif and Lindsay for your timely responsiveness and wonderful house - great space!

Home in Edgartown

What guests are saying

Salty by the Sea

5 out of 5 average rating, 24 reviews2 days ago

We absolutely loved Nicole’s place. It’s in a quiet neighborhood and very easy to get to. We used it as a starting point on some trips to Plymouth and Newport. The house is set up very well, had all the amenities we needed, and was very comfortable. Our kids loved going to the beach every day, which is only a two minute drive away, and easily walkable. Nicole also shared several recommendations with us and she did not disappoint! I’d highly recommend her cottage.

Home in Mattapoisett

What guests are saying

Cape Cod, South Yarmouth July 19-26. Sleeps 8

4.75 out of 5 average rating, 4 reviews33 months ago

Loved the location and the apartment was facing the water, which meant a light cool breeze most of the time all day and night. The 2 bedroom apt was very clean and spacious and the 5 of us did not get in each of our ways. While inside, we did not hear any noise from our next door neighbors and sliding doors silenced any outdoor noise. The AC was cold and very comfortable. Amenities including additional outdoor access to a peaceful water area with picnic tables, Adirondack chairs was a huge plus. Indoor pool helped too with two little ones. Beach parking passes at a discount. Staff was very nice and accommodating. Parking was easy and plenty of spaces. Would recommend and we would stay again.

Condo in Yarmouth

What guests are saying

The Squeeze Inn cottage-15 minute walk to beach!

4.93 out of 5 average rating, 100 reviews7 months ago

We have been coming to Cape Cod for several years and have stayed in the same residential area in South Yarmouth. The Squeeze Inn is by far the best stay we have had! The house is set up comfortable and cozy. The backyard is quiet and peaceful. Sean and Jenn were responsive and checked in halfway during the stay to assure we had all we needed. Looking forward to booking again for annual trip!

Cottage in Yarmouth

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Popular amenities for Chappaquiddick vacation rentals

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Free parking on premises

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Other great vacation rentals in Chappaquiddick

4.99 out of 5 average rating, 142 reviews

A circular arrangement of chairs in various colors surrounds a small stone fire pit. The scene overlooks a serene pond, framed by lush trees and bathed in warm sunlight. Subtle outdoor lighting is positioned along the perimeter.

Cottage in Barnstable

Beach Glass Cottage - Pond Front

MaureenRating, 5 stars1 month ago

My friends and I stay at Maureen’s cottage every February for a winter stitching getaway. The house is perfect for the 3 of us. It has 3 comfortable bedrooms and 2 full baths. The living room is spacious. We love the kitchen and dining table. We set up our stitching gear and stitch the days away until it’s time to say goodbye. There are so many great restaurant choices close by. We highly recommend the Keltic Kitchen a short distance away on rte 28. Perfect breakfast place. We also tried for the first time a very small Thai restaurant, Bangkok Kitchen. The food was delicious and very nice people. Back to Maureen’s Beach Glass Cottage…just a perfect place to stay. The amenity list does not even begin to cover what they have available. It’s the perfect getaway home in my opinion. The one floor living is great for us with 1 of us having mobility issues. We cannot wait to come back. Thank You!

4.7 out of 5 average rating, 56 reviews

The image depicts a sandy beach with gentle waves lapping against a rocky shore. Smooth rocks are partially covered in green moss, and the expansive ocean stretches out under a clear blue sky. The sunlight glimmers on the water's surface.

Cottage in Dennis

Great Cottage - Walk to the Beach! (97)

GriffinRating, 5 stars8 months ago

We had a great time at this cottage. The location is perfect with a two minute walk to the beach and great restaurants at both ends of the street. Close to lots of fun family stuff to do. Just enough space for our four-person family!

4.86 out of 5 average rating, 7 reviews

Home in Mattapoisett

5 Blocks to Beach+Town, Stocked Kitchen, Cozy Beds

DavidRating, 5 stars2 months ago

Caitlin was a wonderful hostess, and the house was very nice. I would definitely recommend if you were going to be in the area.

4.94 out of 5 average rating, 18 reviews

A patio area features several white Adirondack chairs arranged around a small table, inviting relaxation. A pergola is visible, with a dining table set for outdoor meals. The pond is seen in the background, framed by trees and a clear sky.

Home in Mashpee

25 Menemsha Rd., Popponesset, pond & beach views

LisaRating, 5 stars5 months ago

We absolutely enjoyed our stayed. It's beautiful from the pictures online, but when you walk in it has a feel of being at a getaway even better than expected. The view is gorgeous and the home is very well kept and decorated. A big bonus for us was the spacious outdoor hottub. I would definitely feel comfortable booking with them again!

5 out of 5 average rating, 59 reviews

Home in Vineyard Haven

Well-Appointed 3 Bedrm 4 Bathrm w/ 50+ 5* Reviews

ElizabethRating, 5 stars8 months ago

Lisa is an incredible host! She was very responsive and easy to reach. The house was very clean and neat and well equipped to make your stay easy and enjoyable. You can really tell that she cares about the home and the comfort of her guests. The home is located in a very quiet lowkey neighborhood with easy access to town and everything you need either by bike or car. I would definitely stay there again.

4.84 out of 5 average rating, 49 reviews

The kitchen features gray cabinets and stainless steel appliances, including a stove and dishwasher. A white tile backsplash complements the countertops. Countertop appliances and dishware are neatly arranged. Natural light enters through a window, illuminating a patterned rug placed in front of the sink.

Home in Falmouth

Escape to the Cape

RodionRating, 5 stars7 months ago

Ananta was very communicative and proactively helpful. Her residence was very accommodating for a family of 6 plus a cat. We all really enjoyed our stay. P.S. Thank you for the welcome snacks and the plant!

5 out of 5 average rating, 6 reviews

Home in Yarmouth

Yarmouthport house heated pool/hot tub near beach.

DeniziaRating, 5 stars7 months ago

We had an amazing stay at this beautiful home! The host was incredibly friendly and flexible . The home itself was spotless, very well maintained and had everything we needed for a comfortable stay. We really enjoyed our time here and would highly recommend this place to anyone looking for a relaxing and enjoyable stay!