Vacation rentals in Simmons Pond

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Top-rated vacation rentals in Simmons Pond

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

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

4.92 out of 5 average rating, 109 reviews

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!

Guest favorite

Home in Mashpee

4.94 out of 5 average rating, 110 reviews

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!

Top guest favorite

A serene outdoor area features four black Adirondack chairs arranged around a small fire pit on lush green grass. The cottage's charming exterior, highlighted by a wooden deck and American flag, is visible in the background, surrounded by trees.

Home in Sandwich

5 out of 5 average rating, 28 reviews

The Cape Cottage Fireplace * Kid Friendly * PetsOK

DanielRating, 5 stars6 days ago

Ariana was extremely attentive to any questions - the location was ideal and the home was very cozy and comfortable. I would highly recommend this location for a quick relaxing weekend or an extended stay! Thank you for a wonderful long weekend stay!! Best Dan & Mary

Guest favorite

Home in Mashpee

4.93 out of 5 average rating, 44 reviews

Tranquil Cape getaway#2 with AC Kid & Pet friendly

JennRating, 5 stars4 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.

Superhost

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

4.9 out of 5 average rating, 48 reviews

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.

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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

11 Drift

4.67 out of 5 average rating, 21 reviews4 months ago

This is a beautiful, old home that has been remodeled nicely. The kitchen amenities are solid. We hosted a Thanksgiving dinner here for my local family and it was absolutely perfect for the occasion. I saw the previous review about heat issues and mold, but we didn't encounter any of those problems. The heat worked very well on the main floor. It was a little chilly in the upstairs bedroom, but nothing that a portable wall heater couldn't take care of. The beds were super comfortable and everything was very clean. The layout of the bedrooms is a little awkward, but nothing insurmountable. There are some hard-to-navigate stairs that lead to the upstairs bedroom that would be impossible for the very old to navigate, but my teenage kids did just fine getting up there. The host was incredibly responsive and even had warm, homemade sourdough bread waiting for us! John is a wonderful host and this home is a true find.

Home in Westport

What guests are saying

In town Cozy-Cottage-Glam w/ Fab backyard 2bd/2B

4.95 out of 5 average rating, 19 reviews7 months ago

The house is lovely! The yard is the real star here, and the location is fantastic. The only small things I would comment on are providing your own linens (not ideal) and no coffee or anything to last a day upon arrival. But overall, I would recommend it for a nice stay on the island!

Cottage in Oak Bluffs

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 reviews3 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

Coastal Cottage

4.96 out of 5 average rating, 28 reviews2 weeks ago

We had a wonderful stay at Coastal Cottage! The setting was lovely and the house was spotless, very well equipped, and super comfortable with plenty of space for everyone. The outdoor areas were lovely and perfect for relaxing and hanging out. The hosts (Lauren & Mike) were responsive and thoughtful, and the welcome treats were such a nice touch! Great amenities all around—this was an ideal spot for a family and friends gathering. Highly recommend!

Home in Little Compton

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Popular amenities for Simmons Pond vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Simmons Pond

Guest favorite

A well-lit entryway leads to a carpeted staircase, with wooden handrails and light-colored walls. The open kitchen area is visible in the background, complemented by a dining space to the right, enhancing the spacious feel of the home.

Apartment in Marshfield

4.91 out of 5 average rating, 66 reviews

FULLY RENO'D apt w/water views near beach& marina

MatthewRating, 5 stars6 months ago

Space was exactly as listed. Very clean and tons of space. We’d absolutely stay here again. Kelly was SUPER kind and responsive!

Superhost

A sandy beach stretches into the distance, bordered by gentle waves lapping at the shore. Two figures can be seen walking along the water's edge, and sparse grass and small dunes are visible in the background under a clear blue sky.

Home in South Kingstown

5 out of 5 average rating, 18 reviews

Green Hill Getaway

SusanRating, 5 stars8 months ago

This house was spotless. Everything felt clean, the beds, the bathrooms. 5 bedrooms all nice size and clean. No carpets which is fantastic when you allow dogs. So happy to bring my two Bostons. Plenty of supplies and kitchen utensils. Nice backyard and neighborhood. AC worked great. The only thing I would recommend is a door on the outside shower. From CT and we don’t have outdoor showers so it would have been nice to have everyone shower outside. Other than that it was perfect for my family. Loved having the bikes ! Jackie left us wine and snacks totally appreciate it. We had a great week.

Top guest favorite

A two-story, light blue house is shown, featuring a well-maintained landscape with shrubs and small trees. A stone wall borders the property, and a concrete walkway with steps leads to a wooden deck at the entryway.

Apartment in Providence

5 out of 5 average rating, 7 reviews

Beautiful and spacious lovely home

ChrisRating, 5 stars3 weeks ago

Place worked out perfect

Superhost

Three turquoise Adirondack chairs are positioned on a grassy area, offering a view of a natural pathway lined with trees. The scene is brightened by natural light filtering through the leaves, creating a serene outdoor environment.

Home in Wareham

4.93 out of 5 average rating, 14 reviews

Private home, secluded 6 acre lot with water view

JaredRating, 5 stars7 months ago

Rebecca’s house in Wareham was a blessing! She is an attentive and responsive host, any concerns I had she was able to resolve immediately. We found ourselves wishing we had booked a longer stay to enjoy everything there was to offer!! Thank you Rebecca!

Superhost

The spacious rooftop deck features outdoor seating arranged around a coffee table, with a light-colored area rug beneath. Greenery from nearby trees adds a natural touch, while the view extends toward Newport Harbor and distant buildings under a clear blue sky.

Condo in Newport

4.73 out of 5 average rating, 60 reviews

Gorgeous Condo w/Roof Deck, Harbor Views on Thames

AlisonRating, 5 stars8 months ago

Our third time staying at this location and we were thrilled with the beautiful updates/renovations both on the roof deck and common corridor carpet.

Superhost

Home in Falmouth

4.8 out of 5 average rating, 25 reviews

5 Bedroom, Central Air, Close to Beaches and MORE!

CarolRating, 5 stars8 months ago

It is a nice house for a large family. We had between 8-12 there at any points. Close to beaches.

Top guest favorite

A sandy beach extends along the shoreline, leading to calm waters reflecting the clear blue sky. Grassy dunes are visible to one side, while the horizon features distant trees. The beach appears serene and inviting, perfect for leisurely walks and relaxing moments by the water.

Home in Wareham

5 out of 5 average rating, 8 reviews

Amazing views, steps to private beach

SallyRating, 5 stars6 months ago

From the time we stepped into the home we were comfortable. Lots of seating areas. Having 2 kitchens worked perfectly for our large group of women who like to cook. Well stocked kitchens and bathrooms with extras I wouldn’t expect at an Airbnb. The linens and towels were perfect. Lots of pillows. It was chilly out when we arrived but the heater splits took the chill out in less than 20 min. The view is exceptional and walk to beach easy for all age groups. Plenty of parking. I can’t say enough about it and look forward to returning.

Superhost