Cheap Vacations in Anguilla

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Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,266, price is now $1,132 per person
$1,132
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $29,046, price is now $20,424 per person
$20,424
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,981, price is now $2,411 per person
$2,411
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $2,281, price is now $1,895 per person
$1,895
per person
Feb 23 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Price was $2,957, price is now $2,514 per person
$2,514
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,499, price is now $1,283 per person
$1,283
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,987, price is now $1,716 per person
$1,716
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Save 100% on your flight
Price was $5,771, price is now $5,014 per person
$5,014
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Price was $3,478, price is now $3,028 per person
$3,028
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was $3,418, price is now $3,097 per person
$3,097
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)

3-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $1,129, price is now $1,034 per person
$1,034
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Price was $3,936, price is now $3,333 per person
$3,333
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Price was $2,957, price is now $2,514 per person
$2,514
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,283, price is now $1,111 per person
$1,111
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
New York (JFK) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Save 100% on your flight
Price was $5,771, price is now $5,014 per person
$5,014
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Price was $3,478, price is now $3,028 per person
$3,028
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,266, price is now $1,132 per person
$1,132
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was $3,418, price is now $3,097 per person
$3,097
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Price was $6,296, price is now $5,790 per person
$5,790
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Price was $5,221, price is now $4,808 per person
$4,808
per person
Feb 24 - Feb 27
found 19 hours ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,590, price is now $1,502 per person
$1,502
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,391, price is now $1,337 per person
$1,337
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)

4-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
Edwards Guesthouse

Edwards Guesthouse

2.5 out of 5
Price was $1,087, price is now $1,004 per person
$1,004
per person
Feb 16 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $5,424, price is now $4,033 per person
$4,033
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Price was $5,519, price is now $4,573 per person
$4,573
per person
Mar 4 - Mar 8
found 1 hour ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,499, price is now $1,283 per person
$1,283
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Price was $7,275, price is now $6,271 per person
$6,271
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
New York (JFK) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,987, price is now $1,716 per person
$1,716
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Price was $4,608, price is now $3,987 per person
$3,987
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,399, price is now $1,226 per person
$1,226
per person
Mar 4 - Mar 8
found 1 hour ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,351, price is now $1,191 per person
$1,191
per person
Mar 4 - Mar 8
found 1 hour ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $1,206, price is now $1,086 per person
$1,086
per person
Mar 4 - Mar 8
found 1 hour ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was $4,633, price is now $4,205 per person
$4,205
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Price was $7,725, price is now $7,072 per person
$7,072
per person
Feb 16 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)

5-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $1,520, price is now $1,343 per person
$1,343
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $6,416, price is now $4,662 per person
$4,662
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,663, price is now $1,361 per person
$1,361
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip flight included
New York (JFK) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Save 100% on your flight
Price was $4,563, price is now $3,749 per person
$3,749
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Save 100% on your flight
Price was $5,230, price is now $4,315 per person
$4,315
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $2,564, price is now $2,137 per person
$2,137
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Save 100% on your flight
Price was $9,380, price is now $7,869 per person
$7,869
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,745, price is now $1,502 per person
$1,502
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,684, price is now $1,456 per person
$1,456
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was $5,221, price is now $4,699 per person
$4,699
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
4-bed Villa, Pool, Parking

4-bed Villa, Pool, Parking

3.5 out of 5
Price was $6,622, price is now $6,065 per person
$6,065
per person
Feb 26 - Mar 3
found 17 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $2,422, price is now $2,242 per person
$2,242
per person
Feb 17 - Feb 22
found 1 day ago
Roundtrip flight included
New York (JFK) to The Valley (AXA)

6-7 night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $1,521, price is now $1,286 per person
$1,286
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $29,046, price is now $20,424 per person
$20,424
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $2,108, price is now $1,654 per person
$1,654
per person
Mar 9 - Mar 16
found 1 day ago
Roundtrip flight included
New York (JFK) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Save 100% on your flight
Price was $28,620, price is now $22,995 per person
$22,995
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Save 100% on your flight
Price was $7,078, price is now $5,724 per person
$5,724
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,981, price is now $2,411 per person
$2,411
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $2,144, price is now $1,742 per person
$1,742
per person
Mar 8 - Mar 15
found 1 day ago
Roundtrip flight included
New York (JFK) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,835, price is now $1,508 per person
$1,508
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,978, price is now $1,677 per person
$1,677
per person
Feb 21 - Feb 28
found 18 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Save 100% on your flight
Price was $9,635, price is now $8,420 per person
$8,420
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $6,960, price is now $6,269 per person
$6,269
per person
Feb 16 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to The Valley (AXA)
6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Save 100% on your flight
Price was $9,415, price is now $8,577 per person
$8,577
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)

Top places to visit in Anguilla

FlightsFlightsHotelsHotels

West End Village

West End Village

Flight deals to Anguilla

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Apr 6 - Thu, Apr 9
MIA
Miami
AXA
The Valley
$458 Roundtrip, found 6 days ago
$458
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Apr 6 from Miami to The Valley, returning Thu, Apr 9, priced at $458 found 6 days ago
Sun, May 3 - Fri, May 8
EWR
New York
AXA
The Valley
$594 Roundtrip, found 3 days ago
$594
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, May 3 from New York to The Valley, returning Fri, May 8, priced at $594 found 3 days ago
Mon, Mar 9 - Fri, Mar 13
BOS
Boston
AXA
The Valley
$599 Roundtrip, found 3 days ago
$599
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Mar 9 from Boston to The Valley, returning Fri, Mar 13, priced at $599 found 3 days ago

Top rated hotels for your Anguilla vacation

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
6.63 mi from city center
$1,822 nightly
The price is $2,030 total per night
$2,030 total
Feb 9 - Feb 10
Total with taxes and fees
When you stay at Four Seasons Resort and Residences Anguilla in West End Village, you'll be on the beach and 11.3 mi (18.2 km) from Shoal Bay Beach.
Pool
Spa
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Rendezvous Bay Rendezvous Bay
4.67 mi from city center
Get rates
With a stay at Anguilla Great House Beach Resort in Rendezvous Bay, you'll be on the beach, within a 10-minute drive of Meads Bay and Rendezvous Bay Beach.
Pool
Spa
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Maundays Bay Maunday's Bay
6.82 mi from city center
$2,217 nightly
The price is $2,478 total per night
$2,478 total
Jan 18 - Jan 19
Total with taxes and fees
With a stay at Cap Juluca, A Belmond Hotel, Anguilla in Maunday's Bay, you'll be next to a golf course, within a 5-minute drive of Meads Bay and Cove Bay.
On private beach
Pool
Don't see what you're looking for?
See all available properties in Anguilla
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.