Vacation rentals in Chappaquiddick

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, 111 reviews

A cozy family room features a slip-covered sofa and two light-colored armchairs, arranged around a wooden coffee table. A brick fireplace complements the space, and a flat-screen TV is mounted above it. Light from the window illuminates the warm wooden flooring.

Home in Mashpee

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

JobRating, 5 stars3 days ago

This was our first stay at an air bnb. Now the bar is set high. After the second day we caught ourselves saying “let’s get home “ . The neighborhood is friendly and quiet. We were so happy that your place was our first.

4.88 out of 5 average rating, 153 reviews

Home in Yarmouth

* Walk to the beach - Swiss Beach House! *

JennaRating, 5 stars8 months ago

The Swiss House is an ideal retreat for families seeking a harmonious blend of comfort and connection. The expansive open-concept living area downstairs fostered a sense of togetherness, while the well-appointed kitchen made preparing family meals a breeze. Nestled away from the hustle, yet conveniently close to amenities, the house offers a perfect balance of privacy and accessibility. A quick drive to Mayflower Beach added to the allure, making our stay nothing short of delightful.

4.93 out of 5 average rating, 44 reviews

A modern kitchen is showcased with light cabinetry, granite countertops, and stainless steel appliances. Exposed wooden beams enhance the high ceiling. A dining area is visible, featuring a round table surrounded by chairs. Natural light brightens the space, providing a warm, inviting ambiance.

Home in Mashpee

Tranquil Cape getaway#2 with AC Kid & Pet friendly

JennRating, 5 stars1 month 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.

4.8 out of 5 average rating, 56 reviews

An outdoor shower area is highlighted, featuring a clean, white privacy fence and two doors. The stone patio leads to steps that connect to the home, while sunlight illuminates the surroundings, showcasing a manicured grassy space beside the pathway.

Home in Dennis

Walk to Sea St. beach & restaurants - Cape Cod 👙⛱

KaitlinRating, 5 stars8 months ago

This is our second time staying here and we had another great vacation! House is clean and great for our large family. Walkable to ice cream and the beach, can’t ask for more! Looking forward to keeping the tradition going and staying again!

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 stars8 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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Popular amenities for Chappaquiddick vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chappaquiddick

5 out of 5 average rating, 15 reviews

A bright living area features a gray sectional sofa facing large windows, allowing natural light to fill the space. The vaulted wood ceiling adds warmth, while the kitchen is equipped with stainless steel appliances and a wooden dining table, enhancing the open-concept design.

Home in Tisbury

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

DanRating, 5 stars7 months ago

Beautiful house and perfect for our group's time on the Vineyard. This place is a newer house, well-designed and makes an ideal home base for island time. Thanks!

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

A light-filled living area is shown, featuring a cozy sofa, a wooden coffee table, and a television. A kitchenette is visible in the background, complemented by a dining space with two black chairs. Large windows allow for ample natural light, enhancing the open feel of the room.

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!

4.89 out of 5 average rating, 9 reviews

Home in Mattapoisett

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

Pei-TzuRating, 5 stars3 days ago

Lovely house and peaceful and quiet neighborhood.

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 stars8 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!