Holiday rentals in Charlestown

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Top-rated holiday rentals in Charlestown

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

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Top guest favourite
Farm stay in South Kingstown
4.99 out of 5 average rating, 375 reviews

Lavender Farm Private Luxury Suite

The luxury suite features reclaimed wood from a 150 year old silo. Reclaimed beams adorn the ceiling. The shower features rainfall, waterfall and massage jets. There is a four post king size reclaimed wood bed with an amazing second floor view of the entire circular lavender field. There is also an open kitchen/living room area with a view of 4,000+ lavender plants. You will be surrounded by custom-picked imported Italian granite selections. The sinks in the suite feature amethyst geodes.

Guest favourite
The exterior of the vintage cabin features a welcoming porch with two green chairs and various potted plants. The cabin has a clean, white facade with dark doors, surrounded by a lush green lawn and trees, inviting a sense of tranquility.
Guest house in Charlestown
4.88 out of 5 average rating, 329 reviews

Cozy All Season Cabin Near Beach at Rockbriar Farm

Small vintage vacation cabin located in Charlestown, RI a 1 mile walk/bike to the town beach. Located on 7 acres called Rockbriar Farm, the cabin is in a wooded setting away from our home affording privacy for guests. One large room includes the futon bed/couch and the one sink; the shower and toilet are in separate room. Cabin also has a cedar enclosed hot water outdoor shower. Clean, cozy but not luxurious! No stove, but coffee maker, microwave, outside grill, and mini fridge.

Top guest favourite
The exterior view features a partially shaded wooden deck with a gas grill, surrounded by landscaped areas and a variety of shrubs. A smooth stone pathway leads to the entrance, and a grassy area extends beyond, framed by trees in the background.
Flat in South Kingstown
4.95 out of 5 average rating, 155 reviews

Blue Dream BnB

This is a 1,400 sq ft private in-law apartment with your own locked entrance completely separate from the house. The 1st floor has two bedrooms with new queen beds and a full bath. The 2nd floor has a full kitchen, pull out couch, full bath and room for an inflatable bed. Child and dog friendly with pack n play and water bowls on hand. Please look at our reviews to see if we would be a good fit. A few miles from several local beaches, Newport and the Block Island Ferry. 4:20 friendly.

Top guest favourite
An inviting living space is characterized by high post and beam cathedral ceilings, with a floor-to-ceiling fieldstone fireplace as a focal point. Cozy seating is arranged around a central coffee table, with warm lighting provided by string lights. The area reflects a blend of rustic charm and modern comfort.
Cabin in Westerly
5 out of 5 average rating, 170 reviews

Sunny Days, Starry Nights | 10 Min to Beaches

☀️ WESTERLY BEACH PASS INCLUDED ☀️ Welcome to Woodhaus Westerly — Minutes to both Westerly and Charlestown beaches, downtown shops, breweries, and coastal walks. Enjoy a crisp beverage on the front porch swings, cool off in the outdoor shower then take in the stars after dark while enjoying an evening bonfire. Dog + kid friendly with plenty of space to relax. Perfect for couples and families - designed for making summer memories. View more photos and updates @Woodhaus_Properties

Top guest favourite
A bright living space features a white brick fireplace, complemented by a black fire screen. Above the mantel, a large, minimalistic artwork with a sun motif is displayed. Shelving holds neatly stacked firewood and decorative items, enhancing the room's inviting ambience.
Home in Westerly
4.98 out of 5 average rating, 125 reviews

South County House

South County House is a 1500 sq ft two bedroom, 1.5 bath cape built in 1936 that sits on nearly an acre of land, 3/4 of a mile from the ocean in Westerly, RI. It borders preserved forest, and there is a small family farm across the street. The house has been thoughtfully redesigned and renovated with relaxation in mind, and provides an ideal escape from the distractions and noise of modern life. Recently featured in Vogue, Architectural Digest, Travel + Leisure, Remodelista, etc.

Guest favourite
An open living area features a blue sectional sofa positioned near a wooden coffee table. Natural light brightens the space from windows above the kitchen, where bar stools line the counter. A ceiling fan and decorative artwork accent the high ceilings.
Home in Charlestown
4.9 out of 5 average rating, 199 reviews

Spacious RI Beach Escape

Super-cute 3 bedroom, 2 bathroom house with big yard, deck and enclosed outdoor shower. Located on a quiet cul-de-sac just minutes from Charlestown Beach and walking distance to local restaurants and shops. Beautiful sunroom just off the kitchen provides bonus living space. There are multiple spots to comfortably work from home with strong connection for video calls. New Casper mattresses in every bedroom. Perfect for family vacation, a weekend with friends or a long-term stay.

Top guest favourite
A stone staircase descends towards a serene pond, bordered by lush greenery and vibrant hydrangeas in bloom. The calm water reflects the surrounding trees, creating a peaceful natural setting.
Guest suite in Westerly
4.96 out of 5 average rating, 159 reviews

Room with a View on Spring Pond

Fab newly decorated suite in 1957 home set on a private pond near Watch Hill, RI. Private entrance with mini kitchen, fridge,microwave, portable induction cooktop,toaster,coffeemaker- every thing but the kitchen sink! Please note: there is no kitchen sink nor oven. Ensuite bath with new towels,robes,linens,and bedding. Outdoor shower ( in addition to an indoor one!) ,grill,lounging area. Near beaches,music,food, Mystic Ct attractions. Great relaxing venue.

Top guest favourite
Home in Charlestown
5 out of 5 average rating, 35 reviews

Single-Level 4BR | 1 Mi to Beach + Parking Pass

Escape to our peaceful home, perfect for a beach getaway, romantic weekend, family stay, or remote work retreat. Thoughtfully designed with open living spaces, private outdoor areas, and modern comforts. For beach lovers, the pristine Charlestown Beach is one mile away as well as the Ninigret Salt Pond for kayaking & paddleboarding. Our rental comes with the convenience of exclusive Charlestown Beach parking for one car for ease of access.

Top guest favourite
The exterior of the historic barn is featured, showcasing weathered wood siding and a welcoming entrance with double doors. The structure is surrounded by trees and a gravel pathway leading to the front door. Soft morning light highlights the natural beauty of the setting.
Barn in Essex
4.96 out of 5 average rating, 187 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Guest favourite
A waterfront view features calm blue waters extending towards the horizon, framed by a white railing. The sky above is dotted with fluffy clouds, complementing the serene landscape of the pond and surrounding vegetation.
Home in Charlestown
4.9 out of 5 average rating, 113 reviews

Cozy cottage on the water

Escape to our idyllic, air conditioned beach house nestled by Green Hill Pond! Just a quick kayak or bike journey to the beach. Embrace tranquility by the saltwater pond, connected to the ocean. Enjoy essentials nearby - bakery, restaurant, ice cream shop, and grocery store. Begin your day with breakfast on the waterside deck, kayak to the beach, and unwind with serene pond vistas. Dive into a beach escape like no other – book now!

Top guest favourite
Home in Charlestown
4.99 out of 5 average rating, 100 reviews

2 Acre Lakefront Getaway (Sauna/Firepit/Kayaks)

Step into our beloved lakeside haven on Pasquiset Pond, a place where comfort meets tranquility. Whether you're in search of a peaceful retreat or a cozy spot to reconnect with family, our home offers a warm and inviting escape, perfect for any season. When you're ready to explore, you'll discover beautiful beaches just 10-15 minutes away, along with the unique charm and vibrant local culture that make this area special.

Top guest favourite
A charming two-story house is situated amidst greenery, featuring a welcoming front porch with black chairs. The exterior showcases light yellow siding and dark blue shutters. A gravel pathway leads to the entrance, surrounded by lush trees and grass.
Home in South Kingstown
4.97 out of 5 average rating, 207 reviews

Cozy beach house close to beaches with Fire Pit

Escape to our recently renovated (May 2023) beach house! This bright, 3-bedroom home comfortably sleeps your group with king, queen, and bunk beds. Features a modern kitchen, two pristine bathrooms, and a bonus lower-level playroom with a TV and toys. Perfectly located just a 5-minute drive from local beaches, nature reserves, and shops. Ideal for families and groups seeking a coastal adventure.

Popular amenities for Charlestown holiday rentals

When is the best time to visit Charlestown?

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Avg. price$296 SGD$340 SGD$399 SGD$340 SGD$385 SGD$390 SGD$449 SGD$453 SGD$383 SGD$383 SGD$372 SGD$326 SGD
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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Charlestown?

    Four-legged friends are welcome in Charlestown. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Charlestown?

    Yes! Work meets play with ease at over 70 vacation rentals in Charlestown featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Charlestown?

    Charlestown has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cottage rentals in Charlestown?

    Experience the best of Charlestown with our cottage rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Charlestown have air conditioning?

    Absolutely! We offer over 120 house rentals with air conditioning in Charlestown. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Charlestown have wifi?

    Absolutely! We offer over 30 cottage rentals with wifi in Charlestown. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Charlestown have a bbq area?

    Absolutely! We offer over 60 house rentals with a bbq area in Charlestown. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Charlestown?

    Enhance your stay in our House Rentals with the most popular amenities: over 120 homes with air conditioning, over 60 homes with a bbq area, over 120 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Charlestown

  • Total holiday rentals

    Explore 180 holiday rentals in Charlestown

  • Nightly prices starting at

    Charlestown holiday rentals start at $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    150 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    170 of Charlestown holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Charlestown rentals

  • 4.9 Average rating

    Charlestown stays are highly rated by guests – averaging 4.9 out of 5!