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Pirate Cove Cottages - Vacation Rentals in Simsbury

Creekside Hidden Eco Vintage Cottage in Nature Sanctuary From US $256
         

9.6 (4 Reviews)
Cottage
Creekside Hidden Eco Vintage Cottage in Nature Sanctuary
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Places to Stay in Simsbury

Over 98+ Luxury Places to Stay in or Near Simsbury
Ideal Family Stay Sleeps 20 in Bloomfield, CT From US $1,581
         

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House
Ideal Family Stay Sleeps 20 in Bloomfield, CT
  • Air Conditioner
  • Parking
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Spacious House in Prime Location From US $1,581
         

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New
House
Spacious House in Prime Location
  • Air Conditioner
  • Parking
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Mint restored historic Simsbury 4BR estate; optional 1BR apt; all new amenities From US $1,506
         

10.0 (2 Reviews)
House
Mint restored historic Simsbury 4BR estate; optional 1BR apt; all new amenities
  • Air Conditioner
  • Parking
  • TV

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Charming barn in nice Avon with WiFi From US $1,438
         

New
House
Charming barn in nice Avon with WiFi
  • Pet Friendly
  • Security/Safety
  • Child Friendly

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Old, Unlisted From US $1,383
         

New
House
Old, Unlisted
  • Air Conditioner
  • Parking
  • Pet Friendly

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Old, Unlisted From US $1,383
         

New
House
Old, Unlisted
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury 5BR Home in Central Bloomfield Spot From US $828
         

New
House
Luxury 5BR Home in Central Bloomfield Spot
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  • Parking
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Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT From US $812
         

New
House
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
  • Air Conditioner
  • Parking
  • Pet Friendly

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Top-Rated Vacation Rentals with a Pool in Simsbury

Over 26+ Top-Rated Vacation Rentals with a Pool in or Near Simsbury
Mountaintop Horse Farm with Heated Pool From US $293
         

10.0 (34 Reviews)
House
Mountaintop Horse Farm with Heated Pool
  • Air Conditioner
  • Parking
  • Pool

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Historic Farmhouse in Northwest Connecticut. Minutes from Ski Sundown! From US $335
         

10.0 (8 Reviews)
Other
Historic Farmhouse in Northwest Connecticut. Minutes from Ski Sundown!
  • Air Conditioner
  • Parking
  • Pool

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Simsbury 1820 House From US $200
         

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9.2 (1007 Reviews)
Bed & Breakfast
Simsbury 1820 House
  • Air Conditioner
  • Parking
  • Pool

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Simsbury Inn From US $307
         

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9.2 (286 Reviews)
Hotel
Simsbury Inn
  • Air Conditioner
  • Parking
  • Pool

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Residence Inn by Marriott Hartford Avon From US $155
         

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8.8 (423 Reviews)
Hotel
Residence Inn by Marriott Hartford Avon
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The Simsbury Inn From US $185
         

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8.8 (123 Reviews)
Hotel
The Simsbury Inn
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  • Parking
  • Pool

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Everything You Need For The Perfect Vacation! Free Breakfast and Parking! From US $139
         

8.8 (6 Reviews)
Apartment
Everything You Need For The Perfect Vacation! Free Breakfast and Parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Avon Old Farms Hotel From US $146
         

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8.4 (1001 Reviews)
Hotel
Avon Old Farms Hotel
  • Air Conditioner
  • Pool
  • TV

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Pet-Friendly Vacation Rentals in Simsbury

Over 36+ Pet-Friendly Vacation Rentals in or Near Simsbury
Landing Apartments - The Preserve at Great Pond From US $338
         

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New
Apartment
Landing Apartments - The Preserve at Great Pond
  • Air Conditioner
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Stylish Townhome | Perfect for Family Gatherings & Events From US $713
         

10.0 (4 Reviews)
House
Stylish Townhome | Perfect for Family Gatherings & Events
  • Air Conditioner
  • Parking
  • Pet Friendly

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Premium 3-Story Townhome | Perfect for Large Groups From US $426
         

9.4 (6 Reviews)
House
Premium 3-Story Townhome | Perfect for Large Groups
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield From US $753
         

9.0 (6 Reviews)
House
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
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  • Parking
  • Pet Friendly

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The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do From US $543
         

8.6 (4 Reviews)
House
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
  • Parking
  • Pet Friendly
  • TV

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Modern Family Retreat | Near Downtown Hartford | Sleeps 10 From US $413
         

7.6 (4 Reviews)
House
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Old Avon Village From US $291
         

6.2 (10 Reviews)
Apartment
The Old Avon Village
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sun Filled Lake House Living From US $216
         

6.0 (3 Reviews)
House
Sun Filled Lake House Living
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Simsbury

Over 15+ Large Vacation Homes & Villas in or Near Simsbury
Spacious House with King Beds in Prime Location From US $726
         

New
House
Spacious House with King Beds in Prime Location
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The Old Avon 1800 Manor From US $475
         

New
House
The Old Avon 1800 Manor
  • Air Conditioner
  • Pet Friendly
  • TV

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Ultimate West Simsbury 5 Bedroom House Rental with Private Pool and Outdoor Spa From US $796
         

5.0 (4 Reviews)
House
Ultimate West Simsbury 5 Bedroom House Rental with Private Pool and Outdoor Spa
  • Air Conditioner
  • Pool
  • Private Pool

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Spacious Good-Value Accommodation! 4 Cozy Units, Free Breakfast and Parking! From US $808
         

New
Apartment
Spacious Good-Value Accommodation! 4 Cozy Units, Free Breakfast and Parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Comfort and Convenience! 4 Cozy Units w/Free Breakfast and Parking! From US $808
         

New
Apartment
Comfort and Convenience! 4 Cozy Units w/Free Breakfast and Parking!
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  • Parking
  • Pet Friendly

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Modern 3-Floor Townhome | 5BR | Spacious & Stylish Stay From US $756
         

New
House
Modern 3-Floor Townhome | 5BR | Spacious & Stylish Stay
  • Air Conditioner
  • Parking
  • Pet Friendly

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Ensuring a Very Comfortable & Memorable Stay! 3 Cozy Units, Free Breakfast! From US $608
         

New
Apartment
Ensuring a Very Comfortable & Memorable Stay! 3 Cozy Units, Free Breakfast!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Comfortable & Memorable Stay! 3 Cozy Units, Free Breakfast and Parking! From US $607
         

New
Apartment
Comfortable & Memorable Stay! 3 Cozy Units, Free Breakfast and Parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Wheelchair Accessible Vacation Homes in Simsbury

Over 6+ Wheelchair Accessible Vacation Homes in or Near Simsbury
Simsbury 1820 House From US $165
         

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8.7 (244 Reviews)
Hotel
Simsbury 1820 House
  • Air Conditioner
  • Parking
  • TV

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Recently Updated, One Level, Attached Garage, Peaceful, Zen-Minimalist Space. From US $278
         

10.0 (9 Reviews)
House
Recently Updated, One Level, Attached Garage, Peaceful, Zen-Minimalist Space.
  • Air Conditioner
  • Parking
  • TV

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Avon Old Farms Hotel From US $138
         

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8.1 (219 Reviews)
Hotel
Avon Old Farms Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

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Adventure Getaway! 2 Cozy Units, Free Breakfast and Parking! From US $279
         

New
Apartment
Adventure Getaway! 2 Cozy Units, Free Breakfast and Parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Get Ready for Blissful Getaway! 2 Cozy Units, Free Breakfast and Parking! From US $279
         

New
Apartment
Get Ready for Blissful Getaway! 2 Cozy Units, Free Breakfast and Parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Modern Apartment in Prime Location (ID8044X07) From US $81
         

New
Apartment
Modern Apartment in Prime Location (ID8044X07)
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Simsbury Varoom and Airbnb Places to Stay Under $200

Over 14+ Simsbury Varoom and Airbnb Places to Stay Under $200
Landing | Beautiful 2BD, Clubhouse, Gym From US $183
         

New
Apartment
Landing | Beautiful 2BD, Clubhouse, Gym
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Landing | Modern 2BD, Pool, Clubhouse From US $175
         

New
Apartment
Landing | Modern 2BD, Pool, Clubhouse
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Charming Ranch Home, Backyard Sanctuary, GameRoom, Convenient to Town Center From US $184
         

9.8 (114 Reviews)
House
Charming Ranch Home, Backyard Sanctuary, GameRoom, Convenient to Town Center
  • Air Conditioner
  • Parking
  • TV

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Sunny, vintage farmhouse in the center of quintessential New England farm town. From US $173
         

10.0 (5 Reviews)
Other
Sunny, vintage farmhouse in the center of quintessential New England farm town.
  • Air Conditioner
  • Parking
  • TV

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Charming Bloomfield Bungalow 1-bedroom apartment in gorgeous Bloomfield CT WiFi
New
From US $199
         

New
Apartment
Charming Bloomfield Bungalow 1-bedroom apartment in gorgeous Bloomfield CT WiFi
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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Landing at The Pointe at Dorset Crossing - 1 Bedroom in Downtown Simsbury From US $195
         

New
Apartment
Landing at The Pointe at Dorset Crossing - 1 Bedroom in Downtown Simsbury
  • Air Conditioner
  • Pet Friendly
  • Pool

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Modern Apartment in Prime Location (ID7450X1) From US $145
         

New
Apartment
Modern Apartment in Prime Location (ID7450X1)
  • Child Friendly

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Spacious Guest Apartment in the quiet suburbs of Hartford From US $119
         

New
Apartment
Spacious Guest Apartment in the quiet suburbs of Hartford

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Instantly Bookable Vacation Homes in Simsbury

Over 22+ Instantly Bookable Vacation Homes in or Near Simsbury
Newly Renovated 2 Bedroom in Heart of Tariffville From US $308
         

10.0 (2 Reviews)
Apartment
Newly Renovated 2 Bedroom in Heart of Tariffville
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Luxury 4-bedroom house in charming Bloomfield, Secluded, WiFi & Security camera. From US $418
         

10.0 (1 Review)
House
Luxury 4-bedroom house in charming Bloomfield, Secluded, WiFi & Security camera.
  • Air Conditioner
  • Parking
  • TV

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Relaxing Retreat w/Sweet Yard! From US $621
         

New
Apartment
Relaxing Retreat w/Sweet Yard!
  • Air Conditioner
  • Parking
  • Security/Safety

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Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport From US $369
         

New
House
Charming East Granby house with AC and WiFi 3 minutes to Bradley Airport
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  • Parking
  • TV

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Charming 3-bedroom house with wishing well,WiFi and AC in Bloomfield From US $290
         

New
House
Charming 3-bedroom house with wishing well,WiFi and AC in Bloomfield
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy 1-bedroom house in adorable East Granby
New
From US $254
         

New
House
Cozy 1-bedroom house in adorable East Granby
  • Child Friendly

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2 Mi to Talcott Mtn Trails: Spacious Family Home
New
From US $226
         

New
House
2 Mi to Talcott Mtn Trails: Spacious Family Home
  • Air Conditioner
  • Parking
  • Pool

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Charming & Newly Renovated Apartmentnn From US $212
         

New
Apartment
Charming & Newly Renovated Apartmentnn
  • Air Conditioner
  • Security/Safety
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About Simsbury Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages Simsbury, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Simsbury. Places to stay near Simsbury with prices averaging $256 a night.

Piratecovecottages makes it easy and safe to find and compare vacation rentals in Simsbury with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Simsbury

Type Count
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Simsbury

★ Pro Tip: Piratecovecottages makes it easy to compare the best listings on Piratecovecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Piratecovecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Simsbury.

Weather in Simsbury

View the weather forecast for Simsbury before booking your Simsbury Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Simsbury, CT

Piratecovecottages offers a large selection of top attractions around Simsbury. Research things to do on your vacation before you visit Simsbury.


Rosedale Farms & Vineyards Performing Arts Center at Simsbury Meadows Phelps Tavern Museum Talcott Mountain State Park XL Center Six Flags New England Xfinity Theatre University of Hartford Naismith Memorial Basketball Hall of Fame Connecticut Convention Center MassMutual Center Trinity College Eastern States Exposition MGM Springfield Lake Compounce Big E Springfield Armory Holyoke Mall Connecticut Science Center

Other Places to Stay Near Simsbury, CT


Simsbury Center 93 Properties Phelps Tavern Museum 91 Properties Performing Arts Center at Simsbury Meadows 90 Properties Talcott Mountain State Park 47 Properties Rosedale Farms & Vineyards 28 Properties

Complexes around Simsbury, CT


Simsbury 3 Properties