
Holiday rentals near Elephant's Trunk Flea Market
We found 457 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals within easy reach of Elephant's Trunk Flea Market that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include air conditioning and a pool. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Elephant's Trunk Flea Market
Showing deals for:17 Oct - 24 Oct
Image gallery for Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

1010 out of 10 rating
Exceptional
(18 reviews)
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Danbury, CT
7% off
Price is NZ$12,362
NZ$12,362
NZ$1,766 per night
includes taxes & fees
Image gallery for Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups

1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
Brookfield, CT
16% off
Price is NZ$21,639
NZ$21,639
NZ$3,091 per night
includes taxes & fees
Image gallery for 100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes

1010 out of 10 rating
Exceptional
(10 reviews)
100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes
Roxbury, CT
8% off
Price is NZ$8,895
NZ$8,895
NZ$1,271 per night
includes taxes & fees
Image gallery for Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use

9.69.6 out of 10 rating
Exceptional
(67 reviews)
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
Bethlehem, CT
8% off
Price is NZ$3,011
NZ$3,011
NZ$430 per night
includes taxes & fees
Image gallery for Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

1010 out of 10 rating
Exceptional
(79 reviews)
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!
New Fairfield, CT
11% off
Price is NZ$20,755
NZ$20,755
NZ$2,965 per night
includes taxes & fees
Image gallery for Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball

1010 out of 10 rating
Exceptional
(5 reviews)
Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball
New Fairfield, CT
8% off
Price is NZ$5,125
NZ$5,125
NZ$732 per night
includes taxes & fees
Image gallery for Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!

1010 out of 10 rating
Exceptional
(11 reviews)
Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!
Bethlehem, CT
7% off
Price is NZ$4,438
NZ$4,438
NZ$634 per night
includes taxes & fees
Image gallery for Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

9.89.8 out of 10 rating
Exceptional
(52 reviews)
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Cornwall Bridge, CT
8% off
Price is NZ$9,187
NZ$9,187
NZ$1,312 per night
includes taxes & fees
Image gallery for Charming 1870 cape cottage in Litchfield

1010 out of 10 rating
Exceptional
(51 reviews)
Charming 1870 cape cottage in Litchfield
Litchfield, CT
8% off
Price is NZ$3,271
NZ$3,271
NZ$467 per night
includes taxes & fees
Image gallery for Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!

1010 out of 10 rating
Exceptional
(26 reviews)
Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!
Roxbury, CT
12% off
Price is NZ$2,280
NZ$2,280
NZ$326 per night
includes taxes & fees
Image gallery for A Secluded Modern Getaway

1010 out of 10 rating
Exceptional
(7 reviews)
A Secluded Modern Getaway
Redding, CT
8% off
Price is NZ$11,441
NZ$11,441
NZ$1,634 per night
includes taxes & fees
Image gallery for Litchfield County Four Season Country Paradise

9.69.6 out of 10 rating
Exceptional
(40 reviews)
Litchfield County Four Season Country Paradise
Roxbury, CT
8% off
Price is NZ$13,788
NZ$13,788
NZ$1,970 per night
includes taxes & fees
Image gallery for Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

1010 out of 10 rating
Exceptional
(5 reviews)
Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
New Milford, CT
12% off
Price is NZ$7,719
NZ$7,719
NZ$1,103 per night
includes taxes & fees
Image gallery for Long Meadow Manor, skiing, game room, Apple picking and Lake nearby

1010 out of 10 rating
Exceptional
(14 reviews)
Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
Bethlehem, CT
8% off
Price is NZ$7,627
NZ$7,627
NZ$1,090 per night
includes taxes & fees
Image gallery for Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

1010 out of 10 rating
Exceptional
(7 reviews)
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Sherman, CT
8% off
Price is NZ$6,222
NZ$6,222
NZ$889 per night
includes taxes & fees
Image gallery for Historic Designer City Getaway

1010 out of 10 rating
Exceptional
(9 reviews)
Historic Designer City Getaway
Easton, CT
7% off
Price is NZ$12,705
NZ$12,705
NZ$1,815 per night
includes taxes & fees
Image gallery for Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.
Carmel, NY
19% off
Price is NZ$5,743
NZ$5,743
NZ$820 per night
includes taxes & fees
Image gallery for A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

1010 out of 10 rating
Exceptional
(6 reviews)
A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley
Holmes, NY
8% off
Price is NZ$4,742
NZ$4,742
NZ$677 per night
includes taxes & fees
Image gallery for Woodstove, firepit, lakeviews and access to lake, hiking trails, large terrace!

1010 out of 10 rating
Exceptional
(13 reviews)
Woodstove, firepit, lakeviews and access to lake, hiking trails, large terrace!
Holmes, NY
8% off
Price is NZ$7,088
NZ$7,088
NZ$1,013 per night
includes taxes & fees
Image gallery for Candlewood Cabin - with Private Waterfront

1010 out of 10 rating
Exceptional
(8 reviews)
Candlewood Cabin - with Private Waterfront
New Fairfield, CT
8% off
Price is NZ$4,107
NZ$4,107
NZ$587 per night
includes taxes & fees
Image gallery for FANTASTIC DEAL!! 35% DISCOUNT FOR 1 WEEK STAY - 50% DISCOUNT FOR A 30 DAY STAY

1010 out of 10 rating
Exceptional
(54 reviews)
FANTASTIC DEAL!! 35% DISCOUNT FOR 1 WEEK STAY - 50% DISCOUNT FOR A 30 DAY STAY
Dover Plains, NY
28% off
Price is NZ$12,279
NZ$12,279
NZ$1,754 per night
includes taxes & fees
Image gallery for 6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED

1010 out of 10 rating
Exceptional
(22 reviews)
6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED
Carmel, NY
8% off
Price is NZ$15,994
NZ$15,994
NZ$2,285 per night
includes taxes & fees
Image gallery for Beautiful Lake View House Overlooking Peaceful Whaley Lake

1010 out of 10 rating
Exceptional
(12 reviews)
Beautiful Lake View House Overlooking Peaceful Whaley Lake
Holmes, NY
8% off
Price is NZ$8,349
NZ$8,349
NZ$1,193 per night
includes taxes & fees
Image gallery for Direct Lakefront Home on Lake Lillinonah with Elevator Access

1010 out of 10 rating
Exceptional
(29 reviews)
Direct Lakefront Home on Lake Lillinonah with Elevator Access
Brookfield, CT
8% off
Price is NZ$8,455
NZ$8,455
NZ$1,208 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Elephant's Trunk Flea Market
Showing deals for: 11 Oct - 14 OctCharming 1760 Cape Nestled in the Foothills of Litchfield County
Sleeps 6 · 4 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
152 reviews(152 reviews)
The current price is NZ$1,416
NZ$1,416
for 3 nights, 1 home
NZ$472 per night
includes taxes & fees
Lakeview Cottage with Dock, Kayaks
Sleeps 7 · 3 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The current price is NZ$2,603
NZ$2,603
for 3 nights, 1 room
NZ$868 per night
includes taxes & fees
YOIN: Whispers of Tranquility, a Zen Retreat
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
The current price is NZ$3,173
NZ$3,173
for 3 nights, 1 home
NZ$1,058 per night
includes taxes & fees
Charming Lakefront studio with panoramic lake views.
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is NZ$959
NZ$959
for 3 nights, 1 apartment
NZ$320 per night
includes taxes & fees
Creekside Retreat Tent
Sleeps 8 · 1 bedroom · 0+ bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
The current price is NZ$947
NZ$947
for 3 nights, 1 unit
NZ$316 per night
includes taxes & fees
Quiet Historic Retreat
Sleeps 6 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
The current price is NZ$1,396
NZ$1,396
for 3 nights, 1 home
NZ$465 per night
includes taxes & fees
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value