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Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown

Family-friendly holiday home in Jamestown

Photo gallery for Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown

Windward Cottage, view of the property and the large wrap-around porch.
Sitting room: comfortable, bright and airy with skylights and a ceiling fan
Relaxing area to read or watch movies. Permission required to use fireplace.
Kitchen and dining area. Table can expand for larger groups.
Ground floor master BR - new king bed, very light, spacious and breezy bedroom

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Outdoor barbecue
  • Deck or patio

Explore the area

View map
Jamestown, RI
  • Place, Thames Street
    ‪14 min drive‬
  • Place, Newport Mansions
    ‪18 min drive‬
  • Place, Brown University
    ‪47 min drive‬
  • Airport, Providence, RI (PVD-T.F. Green)
    ‪37 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Study

1 Double Futon

2 bathrooms

Bathroom 1

Towels provided · Bathtub or shower · Toilet · Shower only

Bathroom 2

Towels provided · Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Outdoor play area
Garden
Dining area

About this property

Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown

Wouldn't you rather wake up to birdsong than the noise of traffic? This comfortably furnished modest home is a wonderful place to get away from it all! Enjoy plenty of sea breezes, close to charming downtown Jamestown and easy commuting distance to Newport, Providence and Boston.

Set back from East Shore Road, Windward Cottage is a quiet and relaxing 'home away from home', perfect for family holidays and retreats. It is very well appointed for entertaining with a gas range, gas grill, large wrap-around covered porch and well equipped kitchen. A large yard provides room for youngsters to play ball, Frisbee and other outdoor games.

The master bedroom and bathroom are on the ground floor, off the kitchen, but pocket doors offer privacy from the main living area. Upstairs, there is a Queen-bedded guest bedroom and a full bathroom. A third room upstairs provides a separate room with a double futon, bureau and desk suitable for an office or a children’s bedroom. The fireplace and vaulted ceiling in the sitting room offers a spacious area for reading and socializing.

No stone has been left unturned to offer simple comfort...






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Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
During the summer months, use of the fireplace and firewood is strictly prohibited. Fireplace use during any other time must be requested.

Important information

You need to know

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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
Property Registration Number 03/26/2025, RE.03713-STR

About the area

Jamestown

Jamestown is home to this holiday home. Newport Mansions and The Breakers are notable landmarks, and travellers looking to shop may want to visit Thames Street. Travelling with kids? Consider Warzone Paintball & Airsoft Park and International Tennis Hall of Fame and Museum. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Jamestown, RI

What's nearby

  • Thames Street - 14 min drive - 16.9 km
  • Newport Mansions - 18 min drive - 18.9 km
  • Narragansett Beach - 21 min drive - 25.2 km
  • University of Rhode Island - 24 min drive - 28.5 km
  • Brown University - 47 min drive - 60.3 km

Getting around

  • Newport Ferry Station - 20 min drive
  • North Kingstown, RI (NCO-Quonset State) - 25 min drive

Restaurants

  • ‪McDonald's - ‬19 min drive
  • ‪Newport Storm Brewery - ‬16 min drive
  • ‪Umami Buffet - ‬18 min drive
  • ‪Quonset Tavern By The Green - ‬23 min drive
  • ‪Wickford on the Water - ‬15 min drive

Frequently asked questions

Is Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown?

As of 12 April 2026, prices found for a 1-night stay for 2 adults at Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown on 22 May 2026 start from NZ$562, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown?

On-site parking is available at the property.

What time is check-in at Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown?

Check-in begins at 4:00 PM.

What time is check-out at Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown?

Checkout is at 10:00 AM.

Where is Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown located?

Located in Jamestown, this family-friendly holiday home is 0.2 mi (0.2 km) from Narragansett Bay, and within 9 mi (15 km) of Thames Street and Bannister's Wharf. Mackerel Cove and Fort Wetherill State Park are also within 9 miles (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 46 out of 49 reviews
Rating 8 - Good. 2 out of 49 reviews
Rating 6 - Okay. 1 out of 49 reviews
Rating 4 - Poor. 0 out of 49 reviews
Rating 2 - Terrible. 0 out of 49 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Julie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a lovely property! Just amazing. Accommodations are wonderful. Clean, well maintained, quiet and quaint. Exactly what I’d expect for a Jamestown rental. And the host is outstanding! This is as great a property for families with kids as it is for all adults.
Stayed 7 nights in Oct 2025
Verified

10/10 Excellent

Bettina N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Didn’t want to leave!

Perfect stay. Stocked with every detail!
Stayed 9 nights in Jul 2024
Verified

10/10 Excellent

Ken B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Newport Trip

Wonderful place to relax after a day of sightseeing.
Stayed 7 nights in Sep 2023
Verified

10/10 Excellent

John S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great getaway

We loved our time at Annlee’s house. It was very cozy with a great yard and easy driving to the beach!
Stayed 10 nights in Aug 2023
Verified

10/10 Excellent

Evangelia P.

Liked: Check-in, communication, location, listing accuracy

Jamestown vaca

We enjoyed the Windward cottage very much. It was a relaxing vacation considering we got a few rainy days. Close to Jamestown village and Newport for exploring and some shopping. Great family place.
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

John W.

The Windward Cottage is absolutely charming, quiet and comfortable.

We have been coming to the South County area for many years to spend time at our favorite places; Beavertail Lighthouse, Wickford, Narragansett and Newport, Windward Cottage was perfectly located for our daily travels.
Stayed 7 nights in Aug 2018
Verified

10/10 Excellent

Shirley S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great cottage in the woods

Great place to stay for four adults. Comfortable beds, kitchen is nice with plenty of tools for cooking. Saw deer, groundhogs, and lots of birds on the property. Easy to get to downtown Jamestown and Newport. Would be glad to rent again if in the area.
Stayed 6 nights in Aug 2024
Verified

8/10 Good

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoyed

Good for children and adults
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

Heather B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved it!

Loved our stay in the cottage, owner was super accommodating and perfect with communication. Everything was very clean.
Stayed 4 nights in Oct 2023
Verified

10/10 Excellent

Julia W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect stay in a cozy home

My wife and I loved staying at Annlee’s house! The house was clean and cozy, and perfect to come back to after busy days out and about. Communication with Annlee was easy and questions I had were responded to almost immediately. If we’re ever back in Jamestown we’ll definitely be staying here again!
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Amy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing rental with awesome owner

Owner had great communication with me. There was an issue with some burned out lights and she was on it immediately! I can’t recommend this property enough. It’s clean, cozy, comfortable, and a quiet location. Very convenient for traveling throughout Rhode Island and Connecticut.
Stayed 5 nights in Sep 2023
Verified

10/10 Excellent

Betty W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very pleasant

My sister and I had a great week in the cottage. Everything we needed was around for us. When I needed a band-aid and ointment, there it was. Fantastic! I would certainly come back.
Stayed 7 nights in Sep 2023
Verified

10/10 Excellent

Vicki G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful Beach Retreat

If you are looking to live like a local, this is the property for you. This charming beach cottage is ideally located on a wooded lot with a wide porch to enjoy coffee or a cocktail and watch for deer and bunnies. Yet, the cute downtown and easily accessible town beach are 10 minutes down the road. An exceptionally well-equipped kitchen, comfy beds (and bedroom a/c) and lots of linens made it easy to relax. Annlee was prompt and detailed with communication. We thoroughly enjoyed our stay.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Susan and Larry V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable Stay in Jamestown

We were looking for a week away. We thoroughly enjoyed our stay. We kept the windows open almost all the time. It was sooo pleasant. We had heard that there might be bugs, but that was never a problem. We went for walks along the rocky beach, the roads. We rode our bicycles over half way to the main town. We went to Slice of Heaven a bunch of times. Went to Beavertail. It was great.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

angela m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic home and host!!

As a frequent user of home rentals I can say this was one of the most comfortable, well appointed and clean homes in which I have stayed. It was beautiful and such a peaceful location. The porch surrounding the home is absolutely lovely! More than the home, the rental experience was the most pleasant I’ve had. Annlee made it so easy to check in, she went above and beyond to make sure we had everything we needed to enjoy our stay. She was super responsive and available to answer any questions we had. The house is stocked with everything you need - which is very generous - you do not find that with most rentals. Annlee was a joy to work with, anticipating our needs and working to make it a wonderful stay. I thoroughly enjoyed communicating with her. I highly recommend this home and hope to return.
Stayed 3 nights in Sep 2019
Archival

8/10 Good

A Week in Heaven

Windward Cottage combines more than adequate living space with great outdoor accomodations with its very wide and extensive half wrap around covered porch. We spent a good deal of our time out there with NO MOSQUITOES, at least not at the end of August. Jamestown and Conanicut Island have rich histories dating from the 1630s, the Revolutionary War, but recovered and became a fashionable summer retreat while maintaining a near self supporting country atmosphere. Now with two bridges one can have his and her choices of what to do and explore in addition to the old forts and lighthouses on the island. The cottage offers communal living and kitchen rooms but private bed and bath spaces. A nice lawn surrounds the house in a quiet area of the the North End of the island. The owner could not be more congenial in working with us in the rental process and afterwards.
Verified

6/10 Okay

Kara C.

Liked: Cleanliness, check-in, location
Disliked: Listing accuracy

Quaint but not for us

House is quaint but wasn’t for my family. We were hoping for a cute cottage and a bedroom with an ocean view. This place does not have any ocean views. Porch is cute but we encountered multiple wasp nests so sitting outside was not ideal. Kitchen is well equipt with staples available for use. Cottage shares a driveway with neighbor who had an old bus and a boat in the yard which was the view from the living room. We felt the living room furniture was uncomfortable and the fireplace was not available for use. Also, despite that it’s set back from the road and somewhat private, the curtain situation didn’t really work well. With window unit ACs, the window to floor curtains didn’t work very well if you want the AC on (which we did because it was humid and August) so it was leave the curtains open or tie them up. And the master curtain didn’t close completely. Annlee seemed easy to deal with when we first communicated and then changed her tune once I voiced my concerns. It was the first time I had to deal with this and it put a damper on our vacation. Owner felt that making comments like “Clearly, it is impossible to make some people happy, but unfortunately, I accepted your booking which has caused me lost income - and also caused you disappointment. As you can see from my positive reviews, any other family would have been delighted and appreciative of my home, when it looks as if you were expecting the luxury of The Four Seasons!” which made dealing with this even harder. We were by no means expecting the Four Seasons. Different people/families enjoy certain aspects of one home over another, and we were hoping for (any) ocean view and a usable outside porch as the listing stated. Owner did try to make a “gesture of good will” which was “designed to entice” us to stay but obviously very much took it personal when we didn’t want to. I’ve stayed at many VRBO homes without any problems. Just feel potential renters should know what to expect.
Stayed 3 nights in Aug 2019
Verified

10/10 Excellent

Mandy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A great place to stay!

Great location, comfortable and spacious home which has everything one might need to have a wonderful vacation. This is our second year staying here and we are already looking forward to our visit next year! Annlee is a most accommodating host who is very helpful and easy to communicate with.
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

Mandy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent experience

We couldn’t have wished for a better space for our visit. Annlee is a very thoughtful and helpful host, going above and beyond what one would expect.
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great week in Jamestown

My family of four had a wonderful week at Annlee's cottage in Jamestown. The house is nicely set up and stocked with all the essentials and more. As other reviewers have mentioned, the wrap-around porch is a delightful spot for breakfast and afternoon/evening wine and crackers and watching the deer and birds. Annlee was a great host and provided excellent recommendations and communications while we were there. The few issues we had were addressed quickly and thoroughly. She is a very responsive host and clearly takes pride in providing a great stay to her guests. The house is on the quieter side of the island but only a short drive into town and not far at all to Newport. We enjoyed renting SUP/paddleboards from Jamestown Outdoors, tours of the Newport mansions and a wonderful boat tour on the Temma antique boat! The sunsets from Marsh Meadows were absolutely amazing. Don't miss the delicious sandwiches from Slice of Heaven bakery.
Stayed 7 nights in Aug 2020
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

fine

wildlife fun
Stayed 7 nights in Aug 2020
Verified

10/10 Excellent

Vida C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding weekend

Stayed at the cottage with one other couple and there was plenty of room for the four of us. Annlee made sure everything was just right for our arrival, allowing us early check in and having the kitchen stocked with basic staples. The kitchen was well equipped with a Jennair range and really quiet dishwasher. The showers were great, the beds very comfortable. It was the perfect place to come ‘home’ to after being out all day.
Verified

10/10 Excellent

ted m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very nice

Excellent
Verified

10/10 Excellent

Roy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Home away from home!

Our stay on Conanicut Island was absolutely wonderful! The house was spotless and everything was orderly and easy to find. It was located in a nice quiet neighborhood with lots of privacy. The wrap-around porch was a nice amenity and a great place to relax while watching the deer that visited us each evening. The property owner, Annalee, was very nice and accommodating. She was accessible by phone or text and answered any questions that we had. She also provided information on local attractions as well as great places to eat!! The house is only minutes away from the beach, shopping, and fine cuisine. Highly recommend this jewel!!
Stayed 4 nights in Aug 2019
Verified

10/10 Excellent

Michelle M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Private, secluded spot

No ocean views, but the house is tucked away at the edge of the forest, and makes for some great bird watching at the beginning or end of the day. The kids asked repeatedly if we could just move in and live there forever!

About the host

Hosted by Annlee

Host profile image

Why they chose this property

...to be close to the coast, and the rejuvenating seaside after living in a land-locked place for a long time!

What makes this property unique

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