Cheap Vacations in Anguilla

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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
Sandy Ground
Price was $891, price is now $769 per person
$769
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $18,749, price is now $12,311 per person
$12,311
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $3,976, price is now $2,840 per person
$2,840
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,543, price is now $1,208 per person
$1,208
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,145, price is now $955 per person
$955
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,185, price is now $994 per person
$994
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $3,694, price is now $3,157 per person
$3,157
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,448, price is now $1,270 per person
$1,270
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Save 100% on your flight
Price was $8,278, price is now $7,368 per person
$7,368
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $5,563, price is now $5,026 per person
$5,026
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

3-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 $934, price is now $876 per person
$876
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $14,297, price is now $9,469 per person
$9,469
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $4,144, price is now $3,093 per person
$3,093
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Price was $3,417, price is now $2,899 per person
$2,899
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
New York (JFK) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,311, price is now $1,123 per person
$1,123
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Price was $3,513, price is now $3,072 per person
$3,072
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,395, price is now $1,244 per person
$1,244
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,322, price is now $1,189 per person
$1,189
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $5,563, price is now $5,026 per person
$5,026
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $1,176, price is now $1,082 per person
$1,082
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,350, price is now $1,263 per person
$1,263
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $1,600, price is now $1,600 per person
$1,600
per person
Feb 11 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

4-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 $891, price is now $769 per person
$769
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $18,749, price is now $12,311 per person
$12,311
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $3,976, price is now $2,840 per person
$2,840
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,071, price is now $852 per person
$852
per person
Jan 19 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,145, price is now $955 per person
$955
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,185, price is now $994 per person
$994
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $4,740, price is now $4,036 per person
$4,036
per person
Feb 7 - Feb 11
found 20 hours 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
Save 100% on your flight
Price was $3,694, price is now $3,157 per person
$3,157
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,448, price is now $1,270 per person
$1,270
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $6,286, price is now $5,530 per person
$5,530
per person
Feb 7 - Feb 11
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Save 100% on your flight
Price was $8,278, price is now $7,368 per person
$7,368
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Price was $6,025, price is now $5,512 per person
$5,512
per person
Jan 31 - Feb 4
found 17 hours 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 $1,282, price is now $1,117 per person
$1,117
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $23,151, price is now $14,883 per person
$14,883
per person
Feb 10 - Feb 15
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 $6,175, price is now $4,411 per person
$4,411
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,506, price is now $1,183 per person
$1,183
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $2,405, price is now $1,964 per person
$1,964
per person
Feb 10 - Feb 15
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
Save 100% on your flight
Price was $5,058, price is now $4,146 per person
$4,146
per person
Feb 10 - Feb 15
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 $4,808 per person
$4,808
per person
Feb 6 - Feb 11
found 16 hours 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 $1,646, price is now $1,383 per person
$1,383
per person
Feb 10 - Feb 15
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 $1,525, price is now $1,290 per person
$1,290
per person
Feb 10 - Feb 15
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 $1,583, price is now $1,341 per person
$1,341
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Save 100% on your flight
Price was $17,865, price is now $15,590 per person
$15,590
per person
Feb 6 - Feb 11
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to The Valley (AXA)
4-bed Villa, Pool, Parking

4-bed Villa, Pool, Parking

3.5 out of 5
Save 100% on your flight
Price was $6,406, price is now $5,865 per person
$5,865
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip non-stop 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 $1,231, price is now $1,054 per person
$1,054
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $32,198, price is now $20,623 per person
$20,623
per person
Feb 9 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $8,159, price is now $5,821 per person
$5,821
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,543, price is now $1,208 per person
$1,208
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Save 100% on your flight
Price was $2,610, price is now $2,120 per person
$2,120
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,939, price is now $1,593 per person
$1,593
per person
Feb 9 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,762, price is now $1,455 per person
$1,455
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,627, price is now $1,347 per person
$1,347
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $5,397, price is now $4,599 per person
$4,599
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Save 100% on your flight
Price was $10,019, price is now $8,901 per person
$8,901
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
4-bed Villa, Pool, Parking

4-bed Villa, Pool, Parking

3.5 out of 5
Save 100% on your flight
Price was $7,878, price is now $7,199 per person
$7,199
per person
Feb 9 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $8,985, price is now $8,350 per person
$8,350
per person
Feb 7 - Feb 13
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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, Jan 26 - Fri, Jan 30
DCA
Washington
AXA
The Valley
$471 Roundtrip, found 8 hours ago
$471
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, Jan 26 from Washington to The Valley, returning Fri, Jan 30, priced at $471 found 8 hours ago
Thu, Jan 22 - Tue, Jan 27
JFK
New York
AXA
The Valley
$515 Roundtrip, found 3 hours ago
$515
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Thu, Jan 22 from New York to The Valley, returning Tue, Jan 27, priced at $515 found 3 hours ago
Sun, Jan 25 - Sat, Jan 31
EWR
New York
AXA
The Valley
$515 Roundtrip, found 9 hours ago
$515
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sun, Jan 25 from New York to The Valley, returning Sat, Jan 31, priced at $515 found 9 hours 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
6.06 mi from city center
$1,251 nightly
The price is $1,394 total per night
$1,394 total
Dec 19 - Dec 20
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 10.9 mi (17.6 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
4.66 mi from city center
Get rates
With a stay at Anguilla Great House Beach Resort in Rendezvous Bay, you'll be on the beach, just a 2-minute walk from Rendezvous Bay Beach and 12 minutes by foot from Aurora International Golf Club.
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
$2,580 nightly
The price is $2,884 total per night
$2,884 total
Jan 18 - Jan 19, 2026
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, just a 2-minute walk from Cove Bay and 7 minutes by foot from Maundays 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.