Old Saybrook Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

95 Houses

29

Old Saybrook Cottage w/Fire Pit - Walk to Beach!

Connecticut / Old Saybrook

Old Saybrook cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$184

Responds fast!
avg. 39 minutes

Price per night from

$184

(4) Excellent 

8

Cornfield Point Beachfront Small Cottage

Connecticut / Old Saybrook

Old Saybrook cottage

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$127

Price per night from

$127

31

Old Saybrook 'Nathanial Clarke House' near Harveys

Connecticut / Old Saybrook

Old Saybrook house

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$430

Responds fast!
avg. 39 minutes

Price per night from

$430

7

Marina Point Villas at Saybrook Point

Connecticut / Old Saybrook

Old Saybrook villa

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$915

Price per night from

$915

21

Cornfield Point Beachfront Cottage

Connecticut / Old Saybrook

Old Saybrook cottage

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$417

Price per night from

$417

Great rentals within 20 miles that match your search

Distance approx 4.21 km from Old Saybrook

9

Private 2 Bdrm Cottage, Walk 2 Beach & Riverfront!

Connecticut / Westbrook

Westbrook cottage

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$400

Price per night from

$400

Distance approx 16.2 km from Old Saybrook

(16) Excellent 

21

The Sun, Sand and Relaxation at Hand! Direct Lakefront, Perfect for 2

Mystic Country / Uncasville

Uncasville cottage

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Beach / lakeside relaxation
  • Ask about children
  • Private garden
“Great weekend getaway” My boyfriend and I enjoyed a nice quiet weekend in this lovely cottage. The owner, Victoria, was extremely helpful and accommodating.The view of the lake was the best feature the house had to offer. We really enjoyed having the
…see more

Price per night from

$201

Responds fast!
avg. 1 hour 5 minutes

Price per night from

$201

Distance approx 7.31 km from Old Saybrook

41

New Luxury Waterfront Home

Connecticut / Clinton

Clinton house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$569

Responds fast!
avg. 1 hour 44 minutes

Price per night from

$569

Distance approx 3.98 km from Old Saybrook

24

Updated Old Lyme Cottage - Steps from the Beach!

Connecticut / Old Lyme

Old Lyme cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$172

Responds fast!
avg. 9 minutes

Price per night from

$172

Distance approx 7.64 km from Old Saybrook

24

NEW! Quiet Clinton House Steps to Private Beaches!

Connecticut / Clinton

Clinton house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$201

Responds fast!
avg. 9 minutes

Price per night from

$201

Distance approx 15.26 km from Old Saybrook

(2) Excellent 

30

WATERFRONT Estate on Shelter Island. Fully Renovated. 100 Ft DOCK

Hamptons / Shelter Island

Shelter Island house

4 8 14 nights min

  • 4 bedrooms
  • sleeps 8
  • 14 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$287

Price per night from

$287

Distance approx 15.81 km from Old Saybrook

(1) Excellent 

19

Waterfront Victorian Home

Connecticut / Groton

Groton house

7 12 7 nights min

  • 7 bedrooms
  • sleeps 12
  • 7 nights min
  • Child Friendly
  • Private garden

Price per night from

$571

Price per night from

$571

Distance approx 12.82 km from Old Saybrook

(1) Excellent 

17

Relaxed Village Farmhouse

North Fork / Greenport

Greenport house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Air conditioning
  • Private garden

Price per night from

$458

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$458

Distance approx 11.45 km from Old Saybrook

(6) Excellent 

14

North Fork House with Private Beach Access

North Fork / East Marion

East Marion house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$285

Price per night from

$285

Distance approx 11.88 km from Old Saybrook

(5) Excellent 

23

Beautiful French Country Cottage

North Fork / East Marion

East Marion cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$456

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$456

Distance approx 15.6 km from Old Saybrook

(2) Excellent 

17

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

North Fork / Southold

Southold house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 mi
  • Child Friendly

Price per night from

$428

Price per night from

$428

Distance approx 12.93 km from Old Saybrook

8

Greenport Village Walking Distance to All

North Fork / Greenport

Greenport farmhouse

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$457

Price per night from

$457

Distance approx 18.31 km from Old Saybrook

15

Southold Summer Home for rent

North Fork / Southold

Southold house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$532

Price per night from

$532

Distance approx 16.18 km from Old Saybrook

34

Beach Cottage, Bring The Dog, Founders Landing Beach, Southold, North Fork, NY

North Fork / Southold

Southold house

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 1 mi
  • Child Friendly
  • Air conditioning

Price per night from

$400

Price per night from

$400

Distance approx 18.63 km from Old Saybrook

32

Surrounded By Nature

Connecticut / Guilford

Guilford house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 mi
  • Child Friendly

Price per night from

$192

Price per night from

$192

Distance approx 11.78 km from Old Saybrook

(3) Excellent 

22

Unique English Country Cottage

North Fork / East Marion

East Marion cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$458

Responds fast!
avg. 2 hours 41 minutes

Price per night from

$458

Distance approx 14.5 km from Old Saybrook

(1) Excellent 

28

Bright summer rental "central air" plus beach pass two blocks from ocean beach

Connecticut / New London

New London house

2 12 3 nights min

  • 2 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$273

Responds fast!
avg. 2 hours 14 minutes

Price per night from

$273

Distance approx 17.21 km from Old Saybrook

19

Waterfront Charmer on idyllic Shelter Island

Hamptons / Shelter Island

Shelter Island house

3 8 14 nights min

  • 3 bedrooms
  • sleeps 8
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$1,061

Price per night from

$1,061

Distance approx 19.73 km from Old Saybrook

16

East Hampton Gem

Hamptons / East Hampton

East Hampton house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,603

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$1,603

Distance approx 14.58 km from Old Saybrook

18

North Fork Beach Bungalow

North Fork / Southold

Southold house

5 10 14 nights min

  • 5 bedrooms
  • sleeps 10
  • 14 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$573

Responds fast!
avg. 1 hour 49 minutes

Price per night from

$573

Distance approx 11.72 km from Old Saybrook

(1) Excellent 

21

CHARMING ONE-BEDROOM EFFICIENCY APARTMENT IN THE HEART OF EAST MARION

North Fork / East Marion

East Marion house

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$201

Responds fast!
avg. 2 hours 1 minutes

Price per night from

$201

Distance approx 17.1 km from Old Saybrook

24

NEW! Waterfront Southhold Home w/ Sauna & Dock!

North Fork / Southold

Southold house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$401

Responds fast!
avg. 9 minutes

Price per night from

$401

Distance approx 14.93 km from Old Saybrook

4

Waterfront property by 1801 lighthouse

Connecticut / New London

New London house

4 4 7 nights min

  • 4 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$441

Price per night from

$441

Distance approx 2.44 km from Old Saybrook

10

The Copper Beech Guest House

Connecticut / Old Lyme

Old Lyme house

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$157

Price per night from

$157

Distance approx 12.93 km from Old Saybrook

16

Greenport Village Home Walking Distance to All

North Fork / Greenport

Greenport farmhouse

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$592

Price per night from

$592

Distance approx 11.72 km from Old Saybrook

41

LOVELY LARGE RESTORED FARMHOUSE IN BEAUTIFUL EAST MARION

North Fork / East Marion

East Marion house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$742

Responds fast!
avg. 2 hours 1 minutes

Price per night from

$742

Distance approx 15.57 km from Old Saybrook

19

Southold Contemporary Summer Home Steps from Beach and Vineyard

North Fork / Southold

Southold house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$430

Price per night from

$430

Distance approx 14.62 km from Old Saybrook

(8) Excellent 

21

Sunny 1910 Beach House, Private Beach, Near Casino

Connecticut / New London

New London house

6 13 min stay varies

  • 6 bedrooms
  • sleeps 13
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$299

Price per night from

$299

Distance approx 17.24 km from Old Saybrook

(2) Excellent 

16

Beach House In Wine Country; walk to beach, large sun room, outdoor dining

North Fork / Southold

Southold cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$373

Price per night from

$373

Distance approx 14.43 km from Old Saybrook

21

Private Waterfront W Beach, New Renovation

North Fork / Southold

Southold house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 mi
  • Ask about children

Price per night from

$602

Price per night from

$602

Distance approx 10.91 km from Old Saybrook

15

Modern 3 Bedroom 2 Bath Waterfront House with Private Beach!

North Fork / East Marion

East Marion house

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$537

Price per night from

$537

Distance approx 18.32 km from Old Saybrook

24

Beach Front, spacious 5 Bedrooms, North Fork, Long Island

North Fork / Southold

Southold house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$602

Price per night from

$602

Distance approx 15.54 km from Old Saybrook

24

Fabulous Beach Getaway

Hamptons / Shelter Island

Shelter Island house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$649

Price per night from

$649