Historic Sherman Home on Valley Pond with Pool! 3.2 km from Pawling
Vacation Home in Sherman CT
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Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool    Outdoor Pool  

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Family Getaway with Fireplace in Sherman on 4 Acres! 4.0 km from Pawling
Vacation Home in Sherman CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool    Outdoor Pool  

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New Fairfield Home with Beach Access and Fire Pit 4.8 km from Pawling
Vacation Home in New Fairfield CT
8.7
Very Good
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

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New Milford Home on Candlewood Lake with Dock! 7.2 km from Pawling
Vacation Home in New Milford CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Outdoor Pool  

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High Street Hideaway 8.4 km from Pawling
Vacation Home in New Milford CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Outdoor Pool  

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Heidi's Inn 9.9 km from Pawling
Hotel in Brewster NY
8.9
Excellent
From $150
From $150
Info Categories
Hotel with Swimming Pool

Outdoor Pool  

Hotel near Ski Resorts

Family Friendly Hotel

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Holiday Inn Express Danbury I-84, an IHG Hotel 11.0 km from Pawling
Hotel in Danbury CT
7.2
Good
From $173
From $173
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Hotel near Ski Resorts

Hotel with Swimming Pool

Outdoor Pool  

Hotel near Golf Courses

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Crowne Plaza Danbury, an IHG Hotel 11.3 km from Pawling
Hotel in Danbury CT
8.4
Very Good
Info Categories
Hotel near Ski Resorts

Hotel with Swimming Pool

Heated Pool    Indoor Pool  

Hotel near Golf Courses

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Ethan Allen Hotel 12.1 km from Pawling
Hotel in Danbury CT
7.2
Good
From $59
From $59
Info Categories
Hotel with Swimming Pool

Outdoor Pool  

Outdoor Pool  

Hotel near Ski Resorts
Hotel near Golf Courses

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Residence Inn Danbury 12.3 km from Pawling
Hotel in Danbury CT
8.2
Very Good
From $194
From $194
Info Categories
Hotel near Ski Resorts

Hotel with Swimming Pool

Heated Pool    Indoor Pool  

Hotel with Rooms With Fireplace

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Judd's Bridge Luxurious 5BR Heated Pool, Gas BBQ, PoshPadsCT 12.8 km from Pawling
Vacation Home in Roxbury CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool  

Dog Friendly Vacation Home

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SENTRY HILL 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ PoshPadsCT 12.8 km from Pawling
Vacation Home in Roxbury CT
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Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Private Pool  

Dog Friendly Vacation Home

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Classic Roxbury Home with Picturesque Backyard! 13.8 km from Pawling
Vacation Home in Roxbury CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Outdoor Pool  

Dog Friendly Vacation Home

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Moosehorn 6-BR, Heated Pool, Luxurious! PoshPadsCT 13.9 km from Pawling
Vacation Home in Roxbury CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool  

Vacation Home with Parking

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Calhoun 5BR, Heated Pool, Hot Tub, Gas BBQ, PoshPadsCT 14.2 km from Pawling
Vacation Home in Washington CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool  

Dog Friendly Vacation Home

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Calhoun 4BR, View, Land and Location!! Heated Pool, PoshPadsCT 14.2 km from Pawling
Vacation Home in Washington CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool  

Dog Friendly Vacation Home

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South Street, Mint 4 Bedroom, Heated Pool, Gas BBQ, PoshPadsCT 14.4 km from Pawling
Vacation Home in Washington CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool  

Vacation Home with Parking

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The Mayflower Inn & Spa, Auberge Collection 14.6 km from Pawling
Hotel in Washington CT
10
Excellent
From $1,020
From $1,020
Info Categories
Hotel near Ski Resorts

Hotel with Swimming Pool

Indoor Pool    Outdoor Pool  

Hotel with Spa

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Kielwasser Luxury Barn with Heated Pool, Gas BBQ, Bikes PoshPadsCT 14.6 km from Pawling
Vacation Home in Washington CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool  

Vacation Home with Parking

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Painter Ridge Mint 3 BR with Heated Pool - PoshPadsCT 14.6 km from Pawling
Vacation Home in Roxbury CT
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Private Pool  

Vacation Home with Parking

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*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     Ski (40)
  •     Pool (40)
  •     Private Pool (26)
  •     Heated Pool (19)
  •     Outdoor Pool (18)
  •     Indoor Pool (5)
  •     Parking (28)
  •     Dog Friendly (26)
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  •     Gym (7)
  •     Family (7)
  •     Honeymoon (7)
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  •     Golf (6)
  •     4 Star (5)
  •     Romantic (4)
  •     Free Wi-Fi (2)
  •     Luxury (2)
  •     Rooms with Fireplace (2)
  •     EV charging stations (2)
  •     Spa (2)
  •     Tennis (2)
  •     Yoga (2)
  •     Adult Only (1)
  •     5 Star (1)
  •     Cheap (1)
  •     Boutique-Style (1)
  •     3 Star (1)
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