Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown
House in Jamestown, RI
6 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Includes essentialsGarden, Kitchen or Kitchenette, Air conditioner and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
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...
Keywords:
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...
Keywords:
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Jamestown, RI
$$$$
Ratings and reviews
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
Perfect stay. Stocked with every detail!
10.0 / 10.0
Loved our stay in the cottage, owner was super accommodating and perfect with communication. Everything was very clean.
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
We loved our time at Annlee’s house. It was very cozy with a great yard and easy driving to the beach!
10.0 / 10.0
Wonderful place to relax after a day of sightseeing.
10.0 / 10.0
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.
10.0 / 10.0
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.
8.0 / 10.0
Good for children and adults
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
wildlife fun
10.0 / 10.0
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.
10.0 / 10.0
Excellent
10.0 / 10.0
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.
3.0 / 10.0
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.
10.0 / 10.0
Our family - five adults - rented Annlee's beautiful cottage as a home base for our big pilgrimage to the Newport Folk Festival.
The cottage was wonderful; clean, beautiful, and well-appointed. There is everything you might need during your stay, including bicycles and to-go coffee cups! The blue hydrangeas on the property were really showing off & we even spotted a quite healthy groundhog while sipping our morning coffee. A truly delightful cottage.
We did venture around the island via bicycle. We spent a terrific few hours at the Beavertail Lighthouse & enjoyed the small town island life. Most of our time, however, was spent in Newport. We couldn't resist going to La Maison de Coco everyday for the best scones & coffee. We also loved the White Horse Tavern & Pour Judgement for afternoon cocktails & appetizers.
Jamestown & Newport were enchanting. I would highly recommend the Windward Cottage because of its owner, Annlee. She was an absolute pleasure to work with. She was welcoming, accommodating, and clearly invested in our comfort during our stay. I didn't doubt our accommodations prior to our departure, in part, because of Annlee's attentiveness during the planning process.
Thanks much, Annlee!
Aimee
Indianapolis, Indiana
10.0 / 10.0
We just returned from our second week long summer stay at Windward Cottage. This house is a hidden gem in Jamestown on a beautiful, tranquil and undisturbed island between Narragansett and Newport. Our 7 and 10 year olds loved Jamestown and never ran out activities, from spending picture perfect days at Mackerel Cove town beach (and visiting the Del's Lemonade truck!), climbing the rocky cliffs of Beavertail, sunsets on Sunset Beach, visiting the International Tennis Hall of Fame, and surfing at Narragansett town beach. The food was extraordinary, cooking our own lobsters, fresh bread from Hearth Bakery, and Chopmist Charlies in town. The owner is so thoughtful and has impeccable taste. She always pays attention to the details and was so personally attentive to our needs even while being in Colorado. We love Windward Cottage and recommend it and the region for anyone seeking peace and relaxation without the crowds of Cape Cod or even Newport, which is just a ferry away. We hope to be back again soon for another stay!
10.0 / 10.0
Windward cottage was the perfect retreat. Perfect size for us and our toddler. The house is well-put together with everything you need. It's also in the perfect location - close enough to the town of Jamestown and Newport is easily accessible with the bridge close by - but just far enough away to escape to the quiet. The entire area is beautiful with tons to do.
The owner was attentive and even the neighbors were helpful and very friendly.
We will definitely be going back for an escape from every day life.
10.0 / 10.0
We had a wonderful week at Windward Cottage. The home was immaculate and well appointed, the beds very comfortable and the owner very accommodating. The location was perfect for us - close proximity to Newport and the big wave beaches at Narragansett. Jamestown is a gorgeous, quiet place.
10.0 / 10.0
My family had a gorgeous week at the Windward Cottage on Jamestown Island! The cottage is lovely, quiet, immaculate, and comfortable. We enjoyed sitting out on the chaise or at the table on the wrap-around porch, being surrounded by the New England-style stacked stone wall and beautiful gardens, and the ocean across the street. A short drive into town was fun for dinner and drinks and great music and dancing at the Narragansett Cafe on Friday and Saturday nights; Beavertail lighthouse at the other end of the island was the perfect spot for a picnic and watch the sailboats float on by; and the jaunt over the Newport bridge in minutes brought us antiquing, touring the mansions, the U.S. Tennis Hall of Fame, and fabulous restaurants and beaches! Can't wait to go back next summer! Absolutely the most charming and adorable home we have ever rented!
10.0 / 10.0
We had a wonderful stay at Windward Cottage. The house is charming, very comfortable, and well equipped. The location is quiet and lovely. The owner was a pleasure to rent from - responsive, informative, and very concerned that everything was to our satisfaction. We highly recommend Windward Cottage!
10.0 / 10.0
My family enjoyed a wonderful week at this charming home. Annlee went out of her way to answer questions and help make our stay perfect. The home is immaculate and the king bed is to die for! A bonus was Annlee's charming neighbor who shared lots of information about the area with us and made the stay more special. We especially enjoyed the Tennis Hall of Fame in Newport, SLice of Heaven Restaurant in Jamestown, Beavertail Lighthouse and the small but very interesting fire fighter's museum in Jamestown.
10.0 / 10.0
We had a wonderful week in Windward Cottage. Beautifully furnished and comfortable. Great kitchen and love the wrap around porch. Spent time in Newport just over the bridge.
10.0 / 10.0
We recently returned from an outstanding week at Windward Cottage. The house is beautiful, with just a short walk to the ocean waters with gorgeous views. The property was well maintained, with a wrap around porch and open back yard for the kids to let off some steam. Annlee had gone out of her way to make us feel comfortable, and for that, we were very grateful. We would highly recommend this home to anyone who can appreciate the serenity of Jamestown and the surrounding sights, seafood and salty air. We hope to return in the near future!
10.0 / 10.0
We spent a lovely week in windward cottage. The house was comfortable, practical and the garden very charming. Everything seemed to have been so well planned and we had everything we needed. The owner was hospitable and went out of her way to help us have a nice vacation. We could get to the center of Jamestown by car very quickly and trips to Newport were also extremely easy. Our stay was just perfect. I would stay there again.
Melissa
FAQs
How much does this house cost compared to others in Jamestown?
The average price for a rental in Jamestown is $382 per night. This rental is $105 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Charming Private 2+ Bedroom Cottage, North End of Conanicut Point, Jamestown?
We found 11 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, fireplace, and parking.
Explore similar vacation rentals in Jamestown
Explore all rentals in JamestownJamestown travel inspiration
Read our blogGuides
Best Dining in Myrtle Beach: A Food Lover’s Dream
Guides
Best East Coast Beaches and Getaway Locations You Can’t Miss
Budget Travel
7 Most Affordable Snowbird Destinations for 2025
Guides
Top Activities to Try in Panama City Beach, Florida
Guides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida